N-(1,2,5-oxadiazol-3-yl)benzamides and their use as herbicides

ABSTRACT

There are described N-(1,2,5-oxadiazol-3-yl)benzamides of the general formula (I) as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), X, Y, Z and R are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims priority to European patent application 09012169.0 filed Sep. 25, 2009 and U.S. application 61/246,295 filed Sep. 28, 2009, the entire contents of which are incorporated by reference in their entireties.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of broad-leaved weeds and grass weeds in crops of useful plants.

2. Description of Related Art

EP 0 173 657 A1 discloses herbicidal mixtures which contain certain N-(1,2,5-oxadiazol-3-yl)benzamides. That document also describes the compound N-(4-methylfurazan-3-yl)-2,4-dichlorophenylcarboxamide.

However, the herbicidal activity of the herbicidal mixtures and N-(1,2,5-oxadiazol-3-yl)benzamides which are known from that document is frequently not sufficient. It is therefore an object of the present invention to provide further herbicidally active compounds.

SUMMARY OF THE INVENTION

It has now been found that N-(1,2,5-oxadiazol-3-yl)benzamides whose phenyl ring is substituted in the 2-, 3- and 4-position by selected radicals are particularly well suited as herbicides.

A subject matter of the present invention are N-(1,2,5-oxadiazol-3-yl)benzamides of the formula (I) or their salts

in which R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl or heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, X and Z independently of one another are in each case nitro, halogen, cyano, formyl, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂, or heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen, Y is nitro, halogen, cyano, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, CO₂R¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-heteroaryl, O—(C₁-C₆)-alkyl-heterocyclyl, O—(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, tetrahydrofuranyloxymethyl, tetrahydrofuranylmethoxymethyl, O(CH₂)-3,5-dimethyl-1,2-oxazol-4-yl, O(CH₂)₂—O(3,5-dimethoxypyrimidin-2-yl, O(CH₂)-5-pyrrolidin-2-one, O(CH₂)-5-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, or heteroaryl or heterocyclyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, halogen and cyanomethyl, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the 12 last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, rhodano, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR^(S), OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR^(S), OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁵ is methyl or ethyl, n is 0, 1 or 2, s is 0, 1, 2 or 3.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In formula (I) and all the formulae below, alkyl radicals having more than two carbon atoms can be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n-, iso-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, partially saturated or fully unsaturated cyclic radical which contains from 3 to 6 ring atoms, of which 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and which radical can additionally be fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl, 4,5-dihydro-1,2-oxazol-3-yl and oxetanyl.

Heteroaryl is an aromatic cyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and which radical can additionally be fused by a benzo ring. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

Where a group is substituted by a plurality of radicals, this means that this group is substituted by one or more identical or different representatives of the radicals mentioned.

Depending on the nature and the attachment of the substituents, the compounds of the formula (I) may be present as stereoisomers. If, for example, one or more asymmetric carbon atoms are present, there may be enantiomers and diastereomers. There may also be stereoisomers if n is 1 (sulfoxides). Stereoisomers may be obtained from the mixtures resulting from the preparation using customary separation methods, for example by chromatographic separation techniques. It is also possible to prepare stereoisomers selectively by using stereoselective reactions employing optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof embraced by the general formula (I) but not specifically defined.

Preferred compounds of the general formula (I) are those in which

R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, a heterocycle selected from the group consisting of pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, benzisoxazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-triazol-3-yl, 1-ethylbenzimidazol-2-yl, 4-methylthiazol-2-yl, thiophen-2-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, isoxazol-2-yl, isoxazol-3-yl, oxazol-2-yl, oxazol-3-yl, pyrrol-2-yl, pyrrol-3-yl, imidazol-2-yl, imidazol-5-yl, imidazol-4-yl, pyrazol-3-yl, pyrazol-5-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-1-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-thiatriazol-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl and pyridazin-4-yl, which heterocycle is substituted by s radicals selected from the group consisting of methyl, methoxy, trifluoromethyl and halogen, or phenyl which is substituted by s radicals selected from the group consisting of methyl, methoxy, trifluoromethyl and halogen, X and Z independently of each other are in each case nitro, halogen, cyano, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or 1,2,4-triazol-1-yl, Y is nitro, halogen, cyano, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², tetrahydrofuranyloxymethyl, tetrahydrofuranylmethoxymethyl, O(CH₂)-3,5-dimethyl-1,2-oxazol-4-yl, O(CH₂)₂—O(3,5-dimethoxypyrimidin-2-yl, O(CH₂)-5-pyrrolidin-2-one or O(CH₂)-5-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, n is 0, 1 or 2, s is 0, 1, 2 or 3.

Especially preferred compounds of the general formula (I) are those in which R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halogen-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,

X and Z independently of one another are in each case nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R² or 1,2,4-triazol-1-yl, Y is nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², tetrahydrofuranyloxymethyl, tetrahydrofuranylmethoxymethyl, O(CH₂)-3,5-dimethyl-1,2-oxazol-4-yl, O(CH₂)₂—O(3,5-dimethoxypyrimidin-2-yl, O(CH₂)-5-pyrrolidin-2-one or O(CH₂)-5-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the three last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R³ is hydrogen or (C₁-C₆)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3.

Especially preferred compounds of the general formula (I) are also those in which

R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halogen-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, X and Z independently of one another are in each case nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R² or 1,2,4-triazol-1-yl, Y is S(O)_(n)R², 4,5-dihydro-1,2-oxazol-3-yl, 5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl or 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the three last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R³ is hydrogen or (C₁-C₆)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3.

In all of the formulae below, the substituents and symbols have the same definition as described under formula (I), unless otherwise defined.

Compounds according to the invention can be prepared for example by the method specified in scheme 1 by reacting, with base catalysis, a benzoyl chloride (II) with a 4-amino-1,2,5-oxadiazole (III):

The benzoyl chlorides of the formula (II), or the benzoic acids on which they are based, are known in principle and can be prepared for example according to the methods described in U.S. Pat. No. 6,376,429 B1, EP 1 585 742 A1 and EP 1 202 978 A1.

Compounds according to the invention can also be prepared by the method specified in scheme 2 by reacting a benzoic acid of the formula (IV) with a 4-amino-1,2,5-oxadiazole (III):

Dehydrating reagents which are conventionally used for amidation reactions, such as, for example, 1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) and the like may be employed for the activation.

The 4-amino-1,2,5-oxadiazoles of the formula (III) are either commercially available or known or can be prepared analogously to methods known from the literature. For example, 3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared from β-keto esters following the method described in Russian Chemical Bulletin, Int. Ed., Vol. 54, No. 4, p. 1032-1037 (2005):

In the abovementioned formula, R is, for example, an alkyl or phenyl radical. 3-Aryl-4-amino-1,2,5-oxadiazoles can be synthesized for example as described in Russian Chemical Bulletin, 54(4), 1057-1059, (2005) or Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 26B(7), 690-2, (1987):

3-Amino-4-halo-1,2,5-oxadiazoles can be prepared from 3,4-diamino-1,2,5-oxadiazole, which is commercially available, for example by the method described in Heteroatom Chemistry 15(3), 199-207 (2004):

Nucleophilic radicals R can be introduced by substitution of the leaving group L in 3-amino-1,2,5-oxadiazoles of the general formula V as described in Journal of Chemical Research, Synopses, (6), 190, 1985 or in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614, 2004:

Collections of compounds of the formula (I) and/or salts thereof which can be synthesized by the aforementioned reactions can also be prepared in a parallel manner, it being possible for this to take place in a manual, partly automated or completely automated manner. In this connection, it is, for example, possible to automate the reaction procedure, the work-up or the purification of the products and/or intermediates. Overall, this is understood as meaning a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (editor Günther Jung), Verlag Wiley 1999, on pages 1 to 34.

For the parallel reaction procedure and work-up, it is possible to use a series of commercially available instruments, for example Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmer, Waltham, Mass. 02451, USA. For the parallel purification of compounds of the formula (I) and salts thereof or of intermediates produced during the preparation, there are available, inter alia, chromatography apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses listed lead to a modular procedure in which the individual process steps are automated, but between the process steps manual operations have to be carried out. This can be circumvented by using partly or completely integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be acquired, for example, from Caliper, Hopkinton, Mass. 01748, USA.

The implementation of single or several synthesis steps can be supported through the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described here, the preparation of compounds of the formula (I) and salts thereof can take place completely or partially by solid-phase supported methods. For this purpose, individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bonded to a synthesis resin. Solid-phase supported synthesis methods are sufficiently described in the specialist literature, e.g. Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (editor Günther Jung), Verlag Wiley, 1999. The use of solid-phase supported synthesis methods permits a series of protocols known in the literature, which again can be carried out manually or in an automated manner. The reactions can be carried out, for example, by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Both on a solid phase and in liquid phase can the procedure of individual or several synthesis steps be supported through the use of microwave technology. The specialist literature describes a series of experimental protocols, for example in Microwaves in Organic and Medicinal Chemistry (editor C. O. Kappe and A. Stadler), Verlag Wiley, 2005.

The preparation according to the process described here produces compounds of the formula (I) and their salts in the form of substance collections which are called libraries. The present invention also provides libraries which comprise at least two compounds of the formula (I) and their salts.

The compounds of the formula (I) according to the invention (and/or their salts), hereinbelow also referred to together as “compounds according to the invention”, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active compounds act efficiently even on perennial weeds which produce shoots from rhizomes, rootstocks and other perennial organs and which are difficult to control.

The present invention therefore also relates to a method for controlling unwanted plants or for regulating the growth of plants, preferably in crops of plants, where one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). In this context, the compounds according to the invention can be applied for example pre-planting (if appropriate also by incorporation into the soil), pre-emergence or post-emergence. Specific examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without the enumeration being restricted to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds according to the invention are applied to the soil surface before germination, the weed seedlings are either prevented completely from emerging or else the weeds grow until they have reached the cotyledon stage, but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely.

If the active compounds are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage of the point of time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. This is why the present compounds are highly suitable for the selective control of unwanted plant growth in plant stands such as stands of agriculturally useful plants or ornamentals.

Moreover, the compounds according to the invention (depending on their respective structure and the application rate applied) have outstanding growth-regulatory properties in crop plants. They engage in the plants' metabolism in a regulatory fashion and can therefore be employed for the influencing, in a targeted manner, of plant constituents and for facilitating harvesting, such as, for example, by triggering desiccation and stunted growth. Moreover, they are also suitable for generally controlling and inhibiting unwanted vegetative growth without destroying the plants in the process. Inhibiting the vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops since for example lodging can be reduced, or prevented completely, hereby.

By virtue of their herbicidal and plant-growth-regulatory properties, the active compounds can also be employed for controlling harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants are known whose starch content is increased, or whose starch quality is altered, or those where the harvested material has a different fatty acid composition.

It is preferred, with respect to transgenic crops, to use the compounds according to the invention in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum/millet, rice and maize or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

It is preferred to use the compounds according to the invention or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum/millet, rice, cassava and maize or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Conventional methods of generating novel plants which have modified properties in comparison to plants occurring to date consist, for example, in traditional breeding methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases:

-   -   the modification, by recombinant technology, of crop plants with         the aim of modifying the starch synthesized in the plants (for         example WO 92/11376, WO 92/14827, WO 91/19806),     -   transgenic crop plants which are resistant to certain herbicides         of the glufosinate type (cf., for example, EP-A-0242236,         EP-A-242246) or of the glyphosate type (WO 92/00377) or of the         sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),     -   transgenic crop plants, for example cotton, with the capability         of producing Bacillus thuringiensis toxins (Bt toxins), which         make the plants resistant to certain pests (EP-A-0142924,         EP-A-0193259).     -   transgenic crop plants with a modified fatty acid composition         (WO 91/13972).     -   genetically modified crop plants with novel constituents or         secondary metabolites, for example novel phytoalexins, which         bring about an increased disease resistance (EPA 309862,         EPA0464461)     -   genetically modified plants with reduced photorespiration which         feature higher yields and higher stress tolerance (EPA 0305398).     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”)     -   transgenic crop plants which are distinguished by higher yields         or better quality     -   transgenic crop plants which are distinguished by a combination,         for example of the abovementioned novel properties (“gene         stacking”)

A large number of molecular-biology techniques which allow the generation of novel transgenic plants with modified properties are known in principle, see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, “Trends in Plant Science” 1 (1996) 423-431).

To carry out such recombinant manipulations, nucleic acid molecules which allow mutagenesis or sequence changes by recombination of DNA sequences can be introduced into plasmids. For example, base substitutions can be carried out, partial sequences can be removed, or natural or synthetic sequences may be added with the aid of standard methods. To link the DNA fragments to each other, adapters or linkers may be added to the fragments, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y., or Winnacker “Gene and Klone”, VCH Weinheim, 2nd Edition 1996.

For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product. To this end, it is possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, it being necessary for these portions to be long enough to have an antisense effect in the cells. The use of DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them, is also possible.

When expressing nucleic acid molecules in plants, the protein synthesized can be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to link the coding region with DNA sequences which ensure localization in a particular compartment. A person skilled in the art is familiar with such sequences (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules may also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants can be plants of any desired plant species, i.e. not only monocotyledonous, but also dicotyledonous, plants.

Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or the expression of heterologous (=foreign) genes or gene sequences.

It is preferred to employ the compounds according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active compounds.

When the active compounds according to the invention are used in transgenic crops, effects are frequently observed—in addition to the effects on harmful plants which can be observed in other crops—which are specific for the application in the transgenic crop in question, for example a modified or specifically widened spectrum of weeds which can be controlled, modified application rates which may be employed for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and an effect on growth and yield of the transgenic crop plants.

The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dustable powders or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in various ways according to which biological and/or physicochemical parameters are required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dustable powders (DP), seed-dressing products, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulations are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986, Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973, K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1963, McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J., Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, “Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to produce combinations with other pesticidally active compounds, such as, for example, insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a readymix or as a tank mix. Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly in water and, as well as the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are ground finely, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation assistants.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more surfactants of the ionic and/or nonionic type (emulsifiers). The emulsifiers used may, for example, be: calcium alkylarylsulfonate salts such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dustable powders are obtained by grinding the active compound with finely distributed solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants, as have, for example, already been listed above for the other formulation types.

Granules can be prepared either by spraying the active compound onto adsorptive granular inert material or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers.

Water-dispersible granules are prepared generally by the customary processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

To prepare plate granules, fluidized-bed granules, extruder granules and spray granules, see, for example, methods in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff, “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active compound concentration is, for example, from about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation components. In the case of emulsifiable concentrates, the active compound concentration can be from about 1 to 90, preferably from 5 to 80, % by weight. Formulations in the form of dusts comprise from 1 to 30% by weight of active compound, preferably usually from 5 to 20% by weight of active compound; sprayable solutions contain from about 0.05 to 80% by weight, preferably from 2 to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is present in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active compound formulations mentioned optionally comprise the respective customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity.

Based on these formulations, it is also possible to produce combinations with other pesticidally active compounds, such as, for example, insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a readymix or as a tank mix.

Active compounds which can be employed in combination with the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active compounds (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by the chemical name, or by the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. By way of example, one and in some cases a plurality of use forms are mentioned here:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryn, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), di-allate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]-ethanesulfonamide, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, L-glufosinate, L-glufosinate-ammonium, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan, indole acetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, IDH-100, KUH-043, KUH-071, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, methazole, methoxyphenone, methyldymron, 1-methylcyclopropen, methyl isothiocyanate, metobenzuron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogensulfate, monolinuron, monosulfuron, monuron, MT 128, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolat-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazol, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalide, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, sulcotrione, sulf-allate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, TH-547, thenylchlor, thiafluamide, thiazafluoron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds

For application, the formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Preparations in the form of dusts, granules for soil application or granules for broadcasting and sprayable solutions are usually not diluted further with other inert substances prior to application.

The required application rate of the compounds of the formula (I) varies according to the external conditions such as, inter alia, temperature, humidity and the type of herbicide used. It may vary within wide limits, for example between 0.001 and 1.0 kg/ha or more of active substance; however, preferably it is between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. Chemical Examples Synthesis of N-(4-methyl-1,2,5-oxadiazol-3-yl)-4-(methylsulfonyl)-2-nitrobenzamide (example No. 1-18 in the tables)

495 mg (2.02 mmol) of 2-nitro-4-methylsulfonylbenzoic acid and 200 mg (2.02 mmol) of 4-methyl-1,2,5-oxadiazol-3-ylamine are dissolved at room temperature (RT) in 5 ml of CH₂Cl₂ and treated with 0.28 ml (2.02 mmol) of triethylamine, 49 mg (0.40 mmol) of 4-dimethylaminopyridine (DMAP) and 1.93 g (3.03 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 30 h at RT and subsequently washed twice with in each case 5 ml of water. The organic phase is dried over Na₂SO₄ and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 350 mg (53%).

Synthesis of 2-chloro-N-(4-methoxy-1,2,5-oxadiazol-3-yl)-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzamide, (example No. 9-174 in the table)

200 mg (0.58 mmol) of 2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoic acid and 66 mg (0.58 mmol) of 4-methoxy-1,2,5-oxadiazole-3-amine are dissolved in 10 ml of CH₂Cl₂ at RT and treated with 0.08 ml (0.6 mmol) of triethylamine, 14 mg (0.12 mmol) of DMAP and 511 mg (0.87 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 20 h at RT and subsequently washed twice with in each case 5 ml of water. The organic phase is dried over Na₂SO₄ and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 90 mg (33%).

Synthesis of 2-chloro-3-[5-(cyanomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-N-(4-cyano-1,2,5-oxadiazol-3-yl)-4-(ethylsulfonyl)benzamide (example No. 8-120 in the table)

200 mg (0.56 mmol) of 2-chloro-3-[5-(cyanomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-4-(ethylsulfonyl)benzoic acid and 62 mg (0.58 mmol) of 4-methoxy-1,2,5-oxadiazol-3-amine are dissolved in 24 ml of CH₂Cl₂ at RT and treated with 0.08 ml (0.6 mmol) of triethylamine, 14 mg (0.12 mmol) of DMAP and 535 mg (0.84 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 20 h at RT and subsequently washed twice with in each case 10 ml of water. The organic phase is dried over Na₂SO₄ and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 120 mg (45%).

Synthesis of N-(4-benzoyl-1,2,5-oxadiazol-3-yl)-2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzamide (example No. 11-5 in the tables)

204 mg (0.59 mmol) of 2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]-benzoic acid and 111 mg (0.59 mmol) of (4-amino-1,2,5-oxadiazol-3-yl)(phenyl)methanone are dissolved in 10 ml of dichloromethane at RT and treated with 59 mg (0.599 mmol) of triethylamine, 14 mg (0.19 mmol) of DMAP and 561 mg (0.882 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 30 h at RT and subsequently washed twice with in each case 5 ml of water. The organic phase is dried over Na₂SO₄ and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 50 mg (15%).

Synthesis of 2-chloro-N-[4-(4-chlorophenyl)-1,2,5-oxadiazol-3-yl]-4-(methylsulfonyl)benzamide, (example No. 10-4 in the tables)

200 mg (0.85 mmol) of 2-chloro-4-(methylsulfonyl)benzoic acid and 167 mg (0.85 mmol) of 4-(4-chlorophenyl)-1,2,5-oxadiazol-3-ylamine are dissolved in 24 ml of CH₂Cl₂ at RT and treated with 0.12 ml (0.85 mmol) of triethylamine, 21 mg (0.17 mmol) of DMAP and 1814 mg (1.28 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 30 h at RT and subsequently washed twice with in each case 5 ml of water. The organic phase is dried over Na₂SO₄ and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 140 mg (36%).

Synthesis of N-(4-acetamido-1,2,5-oxadiazol-3-yl)-2-chloro-4-(methylsulfonyl)benzamide, (example No. 11-31 in the tables)

173 mg (0.5 mmol) of 2-chloro-4-(methylsulfonyl)benzoic acid and 191 mg (0.505 mmol) of N-(4-amino-1,2,5-oxadiazol-3-yl)acetamide are dissolved in 5 ml of dichloroethane at RT and treated with 0.071 ml (0.5 mmol) of triethylamine, 31 mg (0.25 mmol) of DMAP and 483 mg (0.76 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 24 h at RT and subsequently filtered through a glass frit. The residue is washed twice using in each case 1 ml of CH₂Cl₂. The filtrate is passed over a silica-gel-filled SPE cartridge and eluted twice using in each case 5 ml of a mixture of ethyl acetate/methyl tert-butyl ester (1:1). The organic phase is dried over Na₂SO₄ and evaporated. The residue is purified by preparative HPLC using acetonitrile/water. Yield 16 mg (9%).

The examples mentioned in the tables hereinbelow were prepared analogously to the abovementioned methods or can be obtained analogously to the abovementioned methods. The compounds listed in the tables hereinbelow are very specially preferred.

The abbreviations used are:

Et=ethyl Me=methyl n-Pr=n-propyl i-Pr=isopropyl Pen=pentyl Ph=phenyl Ac=acetyl Bz=benzoyl c-Pr=cyclopropyl

TABLE 1 Compounds of the general formula (I) according to the invention in which R is methyl

No. X Y Z Physical data 1-1 CF₃ OCH₂CON(Me)Et SO₂Me ¹H NMR, CDCl₃, 400 MHz 9.05 (bs, 1H), 8.29 (d, 1H), 7.60 (d, 1H), 4.92 (s, 1H), 4.85 (s, 1H), 3.43 (s, 3H), 3.43 (q, 1H), 3.16 (q, 1H), 2.94 (s, 3H), 2.85 (s, 3H), 2.50 (s, 3H), 1.17 (t, 1.5H), 1.12 (t, 1.5H) 1-2 CF₃ OCH₂CON(Me)Et SO₂Et ¹H NMR, CDCl₃, 400 MHz 9.89 (bs, 1H), 8.25 (d, 1H), 7.59 (d, 1H), 4.41 (s, 1H), 4.33 (s, 1H), 3.66 (q, 2H), 3.43 (q, 1H), 3.16 (q, 1H), 2.93 (s, 1.5H), 2.85 (s, 1.5H), 2.49 (s, 3H), 1.25 (t, 3H), 1.18 (t, 1.5H), 1.12 (t, 1.5H) 1-4 CF₃ 2-(1H-pyrazol-1-yl)- SO₂Me ¹H NMR, CDCl₃, 400 MHz ethoxyl 8.29 (d, 1H), 8.24 (bs, 1H), 7.57 (bd, 1H), 7.52 (d, 2H), 6.31 (t, 1H), 4.62 (s, 4H), 3.07 (s, 3H), 2.49 (s, 3H), 1-5 CF₃ 2-(1H-pyrazol-1-yl)- SO₂Et ¹H NMR, CDCl₃, 400 MHz ethoxyl 8.16 (d, 1H), 7.78 (d, 1H), 7.60 (d, 1H), 7.56 (d, 1H), 6.38 (t, 1H), 4.60-4.68 (m, 4H), 3.21 (q, 2H), 2.32 (s, 3H), 1.12 (t, 3H) 1-6 CF₃ tetrahydrofuran-2-yl- SO₂Me ¹H NMR, CDCl₃, 400 MHz methoxy 8.31 (d, 1H), 8.00 (bs, 1H), 7.55 (d, 1H), 4.38-4.45 (m, 1H), 4.29 (t, 1H), 4.15 (dd, 1H), 3.90 (ddd, 2H), 3.39 (s, 3H), 2.48 (s, 3H), 2.02-2.12 (m, 1H), 1.90-2.00 (m, 2H), 1.62-1.72 (m, 1H) 1-7 CF₃ tetrahydrofuran-2-yl- SO₂Et ¹H NMR, CDCl₃, 400 MHz methoxy 8.26 (d, 1H), 8.22 (bs, 1H), 7.54 (d, 1H), 4.37-4.43 (m, 1H), 4.22 (t, 1H), 4.08-4.13 (m, 2H), 3.90 (ddd, 2H), 3.52-3.60 (m, 2H), 2.50 (s, 3H), 2.04-2.12 (m, 1H), 1.90-1.99 (m, 2H), 1.62-1.71 (m, 1H), 1.24 (t, 3H) 1-8 CF₃ OH SO₂Me ¹H NMR, CD₃OD, 400 MHz 8.18 (d, 1H), 7.34 (d, 1H), 3.35 (s, 3H), 2.44 (s, 3H) 1-9 CF₃ OH SO₂Et ¹H NMR, CDCl₃, 400 MHz 9.90 (s, 1H), 7.93 (d, 1H), 7.83 (bs, 1H), 7.21 (d, 1H), 3.25 (q, 2H), 2.50 (s, 3H), 1.38 (t, 3H) 1-10 CF₃ SH SO₂Me ¹H NMR, CD₃OD, 400 MHz 8.34 (pt, 1H), 7.79 (d, 1H), 3.38 (s, 3H), 2.44 (s, 3H) 1-11 CF₃ SH SO₂Et ¹H NMR, CD₃OD, 400 MHz 8.42 (d, 1H), 7.70 (d, 1H), 3.62 (q, 2H), 2.46 (s, 3H), 1.28 (t, 3H) 1-15 CF₃ SMe SO₂Me ¹H NMR, CD₃OD, 400 MHz 8.58 (d, 1H), 7.97 (d, 1H), 7.55 (d, 1H), 3.58 (s, 3H), 2.59 (s, 3H), 2.46 (s, 3H) 1-16 CF₃ SMe SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.57 (bs, 1H), 8.33 (d, 1H), 7.75 (d, 1H), 3.74 (q, 2H), 2.50 (s, 3H), 1.25 (t, 3H), 1-17 CF₃ S(O)Me SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.53 (d, 1H), 7.92 (d, 1H), 3.45 (s, 3H), 3.40 (s, 3H), 2.48 (s, 3H), 1-24 CF₃ S(O)Me SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.62 (d, 1H), 8.26 (d, 1H), 3.85 (q, 2H), 3.72 (s, 3H), 2.45 (s, 3H), 1.42 (t, 3H), 1-25 CF₃ S(O)₂Me SO₂Me ¹H NMR, CD₃OD, 400 MHz 8.68 (d, 1H), 8.26 (d, 1H), 3.70 (s, 3H), 3.60 (s, 3H), 2.44 (s, 3H) 1-26 CF₃ S(O)₂Me SO₂Et ¹H NMR, CD₃OD, 400 MHz 8.59 (d, 1H), 8.19 (d, 1H), 3.82 (q, 2H), 3.71 (s, 3H), 2.44 (s, 3H), 1.42 (t, 3H), 1-27 CF₃ 2-[(methylsulfonyl)- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz amino]ethoxy 8.11 (d, 1H), 7.35-7.42 (m, 2H), 3.50 (t, 2H), 3.39 (s, 3H), 3.25-3.35 (m, 2H), 2.95 (s, 3H), 2.37 (s, 3H) 1-28 CF₃ 2-[(methylsulfonyl)- SO₂Me ¹H NMR, CD₃OD, 400 MHz amino]ethyl}sulfanyl 8.56 (d, 1H), 7.95 (d, 1H), 3.56 (s, 3H), 3.43 (t, 2H), 3.23 (t, 2H), 2.96 (s, 3H), 2.42 (s, 3H) 1-29 CF₃ 2-[(methylsulfonyl)- SO₂Et ¹H NMR, CD₃OD, 400 MHz amino]ethyl}sulfanyl 8.58 (d, 1H), 8.00 (d, 1H), 3.86 (q, 2H), 3.46 (t, 2H), 3.26 (t, 2H), 3.00 (s, 3H), 2.47 (s, 3H), 1.27 (t, 3H) 1-30 NO₂ O(CH₂)₂OMe OMe ¹H NMR, CDCl₃, 400 MHz 8.35 (bs, 1H), 7.45 (m, 2H), 4.15 (m, 2H), 3.70 (m, 2H), 3.42 (s, 3H), 2.46 (s, 3H), 2.43 (s, 3H) 1-31 NO₂ OMe Me ¹H NMR, DMSO-d₆, 400 MHz 11.64 (s, 1H), 7.72 (d, 1H), 7.67 (d, 1H), 3.82 (s, 3H), 2.41 (s, 3H), 2.31 (s, 3H) 1-32 NO₂ NH₂ OMe 1-33 NO₂ NH₂ SO₂Et 1-34 NO₂ NH₂ Cl ¹H NMR, CDCl₃, 400 MHz 7.72 (s, 1H), 7.59 (d, 1H), 6.83 (d, 1H), 6.49 (s, 2H), 2.53 (s, 3H) 1-35 NO₂ NHMe Cl 1-36 NO₂ NMe₂ Cl ¹H NMR, CDCl₃, 400 MHz 9.79 (bs, 1H), 8.18 (s, br, 1H), 7.60 (d, 1H), 7.46 (d, 1H), 2.82 (s, 6H), 2.42 (s, 3H) 1-37 NO₂ NH₂ Br 1-38 NO₂ NHMe Br 1-39 NO₂ NMe₂ Br 1-40 NO₂ NH₂ F 1-41 NO₂ NHMe F 1-42 NO₂ NMe₂ F 1-43 NO₂ NH₂ SO₂Me 1-44 NO₂ NHMe SO₂Me 1-45 NO₂ NMe₂ SO₂Me 1-46 NO₂ NH₂ 1H-1,2,4- triazol-1- yl 1-47 NO₂ NHMe 1H-1,2,4- triazol-1- yl 1-48 NO₂ NMe₂ 1H-1,2,4- triazol-1- yl 1-49 Me F F ¹H NMR, DMSO-d₆, 400 MHz 11.30 (s, 1H), 7.40-7.60 (m, 2H), 2.50 (s, 3H), 2.39 (s, 3H) 1-50 Me F Cl ¹H NMR, DMSO-d₆, 400 MHz 11.38 (s, 1H), 7.49 (d, 1H), 7.62 (dd, 1H), 2.50 (s, 3H), 2.39 (s, 3H) 1-51 Me SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.40 (s, 1H), 7.81 (d, 1H), 7.74 (d, 1H), 2.68 (s, 3H), 2.41 (s, 3H), 2.33 (s, 3H) 1-52 Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.51 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 3.45 (s, 3H), 2.50 (s, 3H), 2.42 (s, 3H) 1-53 Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.53 (s, 1H), 8.26 (d, 1H), 8.08 (d, 1H), 3.61 (s, 3H), 3.57 (s, 3H), 2.72 (s, 3H), 2.41 (s, 3H) 1-54 Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.52 (bs, 1H), 8.04 (m, 2H), 3.44 (s, 3H), 2.75 (s, 3H), 2.41 (s, 3H) 1-55 Me Cl CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.46 (s, 1H), 7.88 (d, 1H), 7.74 (d, 1H), 2.50 (s, 3H), 2.42 (s, 3H) 1-56 Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 7.88 (m, 2H), 3.07 (s, 3H), 2.87 (s, 3H), 2.42 (s, 3H) 1-57 Me SEt OMe ¹H NMR, CDCl₃, 400 MHz 8.02 (bs, 1H), 7.52 (d, 1H), 6.80 (d, 1H), 3.95 (s, 3H), 2.83 (q, 2H), 2.69 (s, 3H), 2.49 (s, 3H), 1.15 (t, 3H) 1-58 Me NMe₂ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.38 (s, 1H), 7.86 (d, 1H), 7.61 (d, 1H), 3.35 (s, 3H), 2.84 (s, 6H), 2.40 (s, 6H) 1-59 Me NH(CH₂)₂OMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.33 (s, 1H), 7.72 (d, 1H), 7.23 (d, 1H), 5.70 (t, 1H), 3.55 (m, 2H), 3.33 (m, 5H), 2.40 (s, 3H), 2.31 (s, 3H) 1-60 Me O(CH₂)₄OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.45 (bs, 1H), 7.75 (d, 1H), 7.45 (d, 1H), 4.01 (t, 2H), 3.46 (t, 2H), 3.35 (s, 3H), 3.23 (s, 3H), 2.50 (s, 3H), 2.46 (s, 3H), 1.94 (m, 2H), 1.77 (m, 2H) 1-61 Me NH₂ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.28 (s, 1H), 7.57 (d, 1H), 6.88 (d, 1H), 6.06 (bs, 2H), 3.16 (s, 3H), 2.39 (s, 3H), 2.19 (s, 3H) 1-62 Me O(CH₂)₂—O(3,5-di- SO₂Me ¹H NMR, CDCl₃, 400 MHz methoxypyrimidin-2- 8.60 (bs, 1H), 7.80 (d, 1H), 7.45 (d, 1H), yl 5.71 (s, 1H), 4.76 (t, 2H), 4.43 (t, 2H), 3.90 (s, 6H), 3.28 (s, 3H), 2.49 (s, 3H), 2.50 (s, 3H) 1-63 Me O(CH₂)₂—O—NMe₂ Cl ¹H NMR, CDCl₃, 400 MHz 7.88 (bs, 1H), 7.33 (d, 1H), 7.27 (d, 1H), 4.38 (t, 2H), 4.20 (t, 2H), 2.49 (s, 3H), 2.45 (s, 3H), 1.88 (s, 6H) 1-64 Me O(CH₂)₂—NH(CO)NMe₂ Cl ¹H NMR, DMSO-d₆, 400 MHz 11.25 (s, 1H), 7.48 (d, 1H), 7.37 (d, 1H), 6.54 (t, 1H), 3.91 (t, 2H), 3.44 (q, 2H), 2.80 (s, 6H), 2.38 (s, 3H), 2.34 (s, 3H) 1-65 Me O(CH₂)-5-pyrrolidin- Br ¹H NMR, CDCl₃, 400 MHz 2-one 9.44 (bs, 1H), 7.51 (d, 1H), 7.25 (d, 1H), 6.0 (bs, 1H), 4.10 (m, 1H), 3.76-3.89 (m, 2H), 2.47 (s, 3H), 2.44 (s, 3H), 2.30 (m, 3H), 1.88 (m, 1H) 1-66 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl ¹H NMR, CDCl₃, 400 MHz 8.53 (bs, 1H), 8.24 (t, 1H), 7.30 (m, 3H), 4.22 (q, 2H), 4.03 (t, 2H), 3.70 (q, 2H), 2.49 (s, 3H), 2.45 (s, 3H), 1.31 (t, 3H) 1-67 Me O(CH₂)—(CO)NEt₂ Br ¹H NMR, DMSO-d₆, 400 MHz 11.25 (s, 1H), 7.64 (d, 1H), 7.34 (d, 1H), 4.59 (s, 2H), 3.35 (m, 4H), 2.37 (s, 6H), 1.14 (t, 3H), 1.08 (t, 3H) 1-68 Me O(CH₂)-5-2,4- Cl ¹H NMR, DMSO-d₆, 400 MHz dimethyl-2,4- 11.30 (s, 1H), 7.52 (d, 1H), 7.44 (d, 1H), dihydro-3H-1,2,4- 4.90 (s, 2H), 3.35 (m, 6H), 2.38 (s, 3H), triazol-3-one 2.33 (s, 3H) 1-69 Me O(CH₂)-3,5- Cl ¹H NMR, CDCl₃, 400 MHz dimethyl-1,2-oxazol- 8.0 (bs, 1H), 7.39 (d, 1H), 7.33 (d, 1H), 4-yl 4.75 (s, 2H), 2.49 (s, 3H), 2.44 (s, 3H), 2.42 (s, 3H), 2.36 (s, 3H) 1-70 Me O(CH₂)₂—NHCO₂Me Cl ¹H NMR, DMSO-d₆, 400 MHz 11.23 (s, 1H), 7.48 (d, 1H), 7.38 (d, 1H), 3.92 (t, 2H), 3.55 (s, 3H), 3.42 (q, 2H), 2.37 (s, 3H), 2.44 (s, 3H) 1-71 Me 4,5-dihydro-1,2- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz oxazol-3-yl 11.48 (s, 1H), 8.03 (d, 1H), 7.92 (d, 1H), 4.50 (t, 2H), 3.34 (t, 2H), 3.27 (s, 3H), 2.41 (s, 3H), 2.35 (s, 3H) 1-72 Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1H), 7.91 (d, 1H), 7.59 (d, 1H), 3.23 (s, 3H), 2.33 (s, 3H), 2.31 (s, 3H) 1-73 Me OH SO₂Me 1-74 Me O—CH₂—NHSO₂cPr Cl 1-75 Me O(CH₂)₂NHSO2Me SO₂Me 1-76 Me S(O)Me SO₂Me 1-77 Me SMe SO₂Me 1-78 Me SMe OMe 1-79 Me S(O)Me OMe 1-80 Me SO₂Me OMe 1-81 Me SMe Cl 1-82 Me S(O)Me Cl ¹H NMR, CDCl₃, 400 MHz 7.54 (d, 1H), 7.37 (d, 1H), 2.92 (s, 3H), 2.67 (s, 3H), 2.47 (s, 3H) 1-83 Me SO₂Me Cl 1-84 Me [1,4]dioxan-2-yl- SO₂Me methoxy 1-85 Me [1,4]dioxan-2-yl- SO₂Et methoxy 1-86 Me O(CH₂)₄OMe SO₂Et 1-87 Me O(CH₂)₃OMe SO₂Me 1-88 Me O(CH₂)₃OMe SO₂Et 1-89 Me O(CH₂)₂OMe SO₂Me 1-90 Me O(CH₂)₂OMe SO₂Et 1-91 Me S(O)Me SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.05 (d, 1H), 7.76 (d, 1H), 3.36 (s, 3H), 3.16 (s, 3H), 2.91 (s, 3H), 2.52 (s, 3H) 1-92 Me SMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.11 (d, 1H), 7.67 (d, 1H), 3.46 (s, 3H), 2.80 (s, 3H), 2.52 (s, 3H), 2.42 (s, 3H) 1-93 Me SMe OMe 1-94 Me S(O)Me OMe 1-95 Me SO₂Me OMe 1-96 Me SMe Cl ¹H NMR, CDCl₃, 400 MHz 7.44 (d, 1H), 7.42 (d, 1H), 2.75 (s, 3H), 2.49 (s, 3H), 2.37 (s, 3H) 1-97 Me S(O)Me Cl 1-98 Me SO₂Me Cl 1-99 Me SMe Br 1-100 Me SOMe Br 1-101 Me SO₂Me Br 1-102 Me SMe I 1-103 Me SOMe I 1-104 Me SO₂Me I 1-105 Me SEt Cl ¹H NMR, CDCl₃, 400 MHz 7.44 (d, 1H), 7.42 (d, 1H), 2.86 (q, 2H), 2.73 (s, 3H), 2.48 (s, 3H), 1.22 (t, 3H) 1-106 Me SOEt Cl ¹H NMR, CDCl₃, 400 MHz 7.54 (d, 1H), 7.36 (d, 1H), 3.26 (m, 1H), 3.03 (m, 1H), 2.65 (s, 3H), 2.47 (s, 3H), 1.33 (t, 3H) 1-107 Me SO₂Et Cl ¹H NMR, CDCl₃, 400 MHz 7.61 (d, 1H), 7.52 (d, 1H), 3.42 (q, 2H), 2.82 (s, 3H), 2.49 (s, 3H), 1.35 (t, 3H) 1-108 Me SEt Br 1-109 Me SOEt Br 1-110 Me SO₂Et Br 1-111 Me SEt I 1-112 Me SOEt I 1-113 Me SO₂Et I 1-114 Me SEt F 1-115 Me SOEt F 1-116 Me SO₂Et F 1-117 Cl OCH₂(CO)NMe₂ Cl ¹H NMR, CDCl₃, 400 MHz 7.39 (d, 2H), 7.26 (d, 1H), 4.62 (s, 2H), 3.12 (s, 3H), 3.02 (s, 3H), 2.41 (s, 3H) 1-119 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 11.25 (s, 1H), 8.18 (d, 1H), 7.75 (d, 1H), 5.38 (s, 2H), 4.05 (q, 2H), 3.25 (s, 3H), 2.45 (s, 3H) 1-120 Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz dihydro-1,2-oxazol- 11.69 (s, 1H), 8.12 (m, 2H), 5.20 (m, 1H), 3-yl 3.61 (m, 1H), 3.43 (q, 2H), 3.19 (m, 1H), 3.02 (m, 2H), 2.40 (s, 3H), 1.18 (t, 3H) 1-121 Cl CH₂O-tetrahydro- SO₂Me ¹H NMR, CDCl₃, 400 MHz furan-3-yl 8.88 (bs, 1H), 8.02 (d, 1H), 7.62 (d, 1H), 5.11 (m, 2H), 4.36 (m, 1H), 3.92-3.74 (m, 4H), 3.21 (s, 3H), 2.51 (s, 3H), 2.10 (m, 2H) 1-122 Cl CH₂O-tetrahydro- SO₂Me furan-2-yl 1-123 Cl SMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.62 (s, 1H), 8.14 (d, 1H), 7.95 (d, 1H), 3.59 (s, 3H), 2.50 (s, 3H), 2.41 (s, 3H) 1-124 Cl F SMe ¹H NMR, DMSO-d₆, 400 MHz 11.46 (bs, 1H), 7.58 (d, 1H), 7.46 (t, 1H), 2.59 (s, 3H), 2.39 (s, 3H) 1-125 Cl CH₂OCH₂- SO₂Me ¹H-NMR, DMSO-d₆, 400 MHz tetrahydrofuran-2-yl 11.65 (s, 1H), 8.12 (d, 1H), 7.91 (d, 1H), 5.10 (m, 2H), 3.98 (m, 1H), 3.72 (dd, 1H), 3.51-3.63 (m, 3H), 3.30 (s, 3H), 2.40 (s, 3H), 1.89 (m, 1H), 1.79 (m, 2H), 1.53 (m, 1H) 1-126 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 1-127 Cl O(CH₂)-5-pyrrolidin- Cl ¹H NMR, CDCl₃, 400 MHz 2-one 9.49 (bs, 1H), 7.44 (s, 2H), 6.38 (bs, 1H), 4.12 (m, 2H), 3.92 (t, 1H), 2.47 (s, 3H), 2.33 (m, 3H), 1.92 (m, 1H) 1-128 Cl SMe Cl ¹H NMR, DMSO-d₆, 400 MHz 11.42 (s, 1H), 7.23 (d, 1H), 7.181 (d, 1H), 3.30 (s, 3H), 2.39 (s, 3H) 1-129 Cl S(O)Me SO₂Me 1-130 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 1-131 Cl O(CH₂)₂OMe Cl 1-132 Cl O(CH₂)₂OMe SO₂Me 1-133 Cl O(CH₂)₄OMe SO₂Me 1-134 Cl O(CH₂)₄OMe SO₂Et 1-135 Cl O(CH₂)₃OMe SO₂Me 1-136 Cl O(CH₂)₃OMe SO₂Et 1-137 Cl O(CH₂)₂OMe SO₂Me 1-138 Cl O(CH₂)₂OMe SO₂Et 1-139 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 1-140 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 1-141 Cl SO₂Me Me 1-142 Cl SEt Me 1-143 Cl SOEt Me 1-144 Cl SO₂Et Me 1-145 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 1-146 Cl Cl SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.30 (bs, 1H), 8.18 (d, 1H), 7.77 (d, 1H), 3.30 (s, 3H), 2.51 (s, 3H) 1-147 F SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.57 (s, 1H), 7.92 (dd, 1H), 7.81 (dd, 1H), 2.50 (s, 3H), 2.39 (s, 3H) 1-148 F S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.69 (s, 1H), 8.15 (dd, 1H), 7.90 (dd, 1H), 3.14 (s, 3H), 2.40 (s, 3H), 1-149 OMe SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.36 (s, 1H), 7.78 (d, 1H), 7.70 (d, 1H), 3.96 (s, 3H), 2.40 (s, 3H), 2.46 (s, 3H) 1-150 OMe S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.32 (d, 1H), 7.72 (d, 1H), 4.21 (s, 3H), 3.14 (s, 3H), 2.51 (s, 3H) 1-151 OMe SO₂Me CF₃ 1-152 Et NH(CH₂)₂OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.64 (bs, 1H), 7.59 (d, 1H), 7.13 (d, 1H), 3.60 (m, 2H), 3.38 (m, 5H), 3.20 (s, 3H), 2.87 (q, 2H), 2.52 (s, 3H), 1.25 (t, 3H) 1-153 Et F SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.62 (bs, 1H), 7.69 (dd, 1H), 7.49 (dd, 1H), 3.22 (s, 3H), 2.90 (m, 2H), 2.50 (s, 3H), 1.29 (t, 3H) 1-154 Et SMe CF₃ 1-155 CF₃ F SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.75 (s, 1H), 8.32 (t, 1H), 7.90 (d, 1H), 3.50 (s, 3H), 2.39 (s, 3H) 1-156 CF₃ F SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.75 (s, 1H), 8.30 (t, 1H), 7.90 (d, 1H), 3.56 (q, 2H), 2.40 (s, 3H), 1.20 (t, 3H) 1-157 CF₃ O(CH₂)₂OMe SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.33 (bs, 1H), 8.23 (d, 1H), 7.55 (d, 1H), 4.39 (t, 2H), 3.81 (t, 2H), 3.55 (q, 2H), 3.43 (s, 3H), 2.50 (s, 3H), 1.25 (t, 3H), 1-158 CF₃ O(CH₂)₃OMe SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.40 (bs, 1H), 8.21 (d, 1H), 7.54 (d, 1H), 4.29 (t, 2H), 3.56 (t, 2H), 3.43 (q, 2H), 3.36 (s, 3H), 2.49 (s, 3H), 2.13 (quin, 2H), 1.25 (t, 3H) 1-159 CF₃ O(CH₂)₂OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.88 (bs, 1H), 8.29 (d, 1H), 7.54 (d, 1H), 4.42 (t, 2H), 3.82 (t, 2H), 3.46 (s, 3H), 3.40 (s, 3H), 2.48 (s, 3H), 1-160 CF₃ O(CH₂)₃OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.31 (bs, 1H), 8.30 (d, 1H), 7.55 (d, 1H), 4.36 (t, 2H), 3.58 (t, 2H), 3.38 (s, 3H), 3.29 (s, 3H), 2.49 (s, 3H), 2.17 (quin, 2H) 1-161 CF₃ OCH₂CONMe₂ SO₂Me ¹H NMR, CDCl₃, 400 MHz 9.10 (bs, 1H), 8.29 (d, 1H), 7.60 (d, 1H), 4.89 (s, 2H), 3.43 (s, 3H), 2.98 (s, 3H), 2.88 (s, 3H), 2.48 (s, 3H) 1-162 CF₃ OCH₂CONMe₂ SO₂Et ¹H NMR, CDCl₃, 400 MHz 9.35 (bs, 1H), 8.28 (d, 1H), 7.60 (d, 1H), 4.87 (s, 2H), 3.68 (q, 2H), 3.00 (s, 3H), 2.90 (s, 3H), 2.48 (s, 3H), 1.23 (t, 3H) 1-163 CF₃ OCH₂CONMe₂ Cl 1-164 CF₃ OCH₂CONMe₂ Br 1-165 CF₃ OCH₂CONMe₂ I 1-166 CF₃ OCH₂CONMe₂ F 1-167 CF₃ O(CH₂)₂OMe Cl 1-168 CF₃ O(CH₂)₃OMe Cl 1-169 CF₃ O(CH₂)₂OMe Br 1-170 CF₃ O(CH₂)₃OMe Br 1-171 CF₃ O(CH₂)₂OMe I 1-172 CF₃ O(CH₂)₃OMe I 1-173 CF₃ O(CH₂)₂OMe F 1-174 CF₃ O(CH₂)₃OMe F 1-175 CF₃ [1,4]dioxan-2-yl- SO₂Me ¹H NMR, CDCl₃, 400 MHz methoxy 8.59 (bs, 1H), 8.38 (d, 1H), 7.75 (d, 1H), 3.88-3.95 (m, 1H), 3.68-3.85 (m, 4H), 3.55-3.65 (m, 1H), 3.50 (s, 3H), 3.36 (dd, 1H), 3.20 (dd, 1H), 2.94 (dd, 1H), 2.50 (s, 3H) 1-176 CF₃ [1,4]dioxan-2-yl- SO₂Et ¹H NMR, CDCl₃, 400 MHz methoxy 8.62 (bs, 1H), 8.32 (d, 1H), 7.75 (d, 1H), 3.88-3.95 (m, 1H), 3.68-3.82 (m, 6H), 3.56-3.64 (m, 1H), 3.36 (dd, 1H), 3.19 (dd, 1H), 2.92-2.97 (m, 1H), 2.50 (s, 3H), 1.25 (t, 3H) 1-177 CF₃ [1,4]dioxan-2-yl- Cl methoxy 1-178 CF₃ [1,4]dioxan-2-yl- Br methoxy 1-179 CF₃ [1,4]dioxan-2-yl- I methoxy 1-180 CF₃ [1,4]dioxan-2-yl- F methoxy 1-181 Br OMe Br ¹H NMR, DMSO-d₆, 400 MHz 11.43 (s, 1H), 7.83 (d, 1H), 7.38 (d, 1H), 3.85 (s, 3H), 2.40 (s, 3H) 1-182 Br O(CH₂)₂OMe Br ¹H NMR, CDCl₃, 400 MHz 8.17 (bs, 1H), 7.65 (d, 1H), 7.30 (d, 1H), 4.22 (m, 2H), 3.85 (m, 2H), 3.47 (s, 3H), 2.50 (s, 3H) 1-183 Br O(CH₂)₄OMe SO₂Me 1-184 Br O(CH₂)₄OMe SO₂Et 1-185 Br O(CH₂)₃OMe SO₂Me 1-186 Br O(CH₂)₃OMe SO₂Et 1-187 Br O(CH₂)₂OMe SO₂Me 1-188 Br O(CH₂)₂OMe SO₂Et 1-189 Br [1,4]dioxan-2-yl- SO₂Me methoxy 1-190 Br [1,4]dioxan-2-yl- SO₂Et methoxy 1-191 Br SMe Me 1-192 Br SOMe Me 1-193 Br SO₂Me Me 1-194 Br SEt Me 1-195 Br SOEt Me 1-196 Br SO₂Et Me 1-197 I O(CH₂)₄OMe SO₂Me 1-198 I O(CH₂)₄OMe SO₂Et 1-199 I O(CH₂)₃OMe SO₂Me 1-200 I O(CH₂)₃OMe SO₂Et 1-201 I O(CH₂)₂OMe SO₂Me 1-202 I O(CH₂)₂OMe SO₂Et 1-203 I [1,4]dioxan-2-yl- SO₂Me methoxy 1-204 I [1,4]dioxan-2-yl- SO₂Et methoxy 1-205 I SMe Me 1-206 I SOMe Me 1-207 I SO₂Me Me 1-208 I SEt Me 1-209 I SOEt Me 1-210 I SO₂Et Me 1-211 CH₂SMe OMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 7.88 (d, 1H), 7.66 (d, 1H), 4.04 (s, 2H), 3.97 (s, 3H), 3.33 (s, 3H), 2.41 (s, 3H), 2.05 (s, 3H) 1-212 CH₂OMe OMe SO₂Me 1-213 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me ¹H NMR, CDCl₃, 400 MHz 9.79 (bs, 1H), 7.95 (d, 1H), 7.38 (d, 1H), 4.65 (s, 2H), 3.75 (m, 2H), 3.51-3.67 (m, 8H), 3.19 (s, 3H), 3.18 (s, 3H), 2.46 (s, 3H), 1.23 (t, 3H) 1-214 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 1-215 CH₂O(CH₂)₃OMe OMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.36 (s, 1H), 7.92 (d, 1H), 7.61 (d, 1H), 4.69 (s, 2H), 3.92 (s, 3H), 3.45 (t, 2H), 3.34 (s, 3H), 3.25 (t, 2H), 3.10 (s, 3H), 2.40 (s, 3H), 1.64 (m, 2H) 1-216 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 1-217 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 1-218 SO₂Me NH₂ CF₃ 1-219 SO₂Me F CF₃ 1-220 SO₂Me NHEt Cl 1-221 SMe SEt F 1-222 SMe SMe F ¹H NMR, DMSO-d₆, 400 MHz 11.20 (s, 1H), 7.55 (dd, 1H), 7.42 (dd, 1H), 2.40 (s, 3H) 1-223 Me NH₂ Cl 1-224 Me NH₂ Br 1-225 Me NHMe Cl 1-226 Me NHMe Br 1-227 Me NMe₂ Cl ¹H NMR, CDCl₃, 400 MHz 7.80 (bs, 1H), 7.28 (d, 1H), 7.26 (d, 1H), 2.88 (s, 6H), 2.49 (s, 3H), 2.47 (s, 3H) 1-228 Me NMe₂ Br ¹H NMR, CDCl₃, 400 MHz 7.75 (bs, 1H), 7.50 (d, 1H), 7.18 (d, 1H), 2.88 (s, 6H), 2.49 (s, 3H), 2.47 (s, 3H) 1-227 Me NMe₂ Cl 1-228 Me NMe₂ Br 1-229 NO₂ O(CH₂)₂OMe Me ¹H NMR, CDCl₃, 400 MHz 8.34 (bs, 1H), 7.46 (d, 1H), 7.44 (d, 1H), 4.15 (t, 2H), 3.70 (t, 2H), 3.41 (s, 3H), 2.46 (s, 3H), 2.41 (s, 3H) 1-230 CF₃ S(O)₂Et SO₂Me ¹H NMR, CD₃OD, 400 MHz 8.69 (d, 1H), 8.25 (d, 1H), 4.00 (bs, 2H), 3.60 (s, 3H), 2.44 (s, 3H), 1.55 (t, 3H) 1-231 CF₃ S(O)₂Et SO₂Et ¹H NMR, CD₃OD, 400 MHz 8.63 (d, 1H), 8.25 (d, 1H), 3.99 (bs, 2H), 3.84 (q, 2H), 2.43 (s, 3H), 1.55 (t, 3H), 1.42 (t, 3H) 1-232 CF₃ SCH₂CONMe₂ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 8.48 (d, 1H), 8.09 (d, 1H), 4.04 (s, 2H), 3.60 (s, 3H), 2.91 (s, 3H), 2.85 (s, 3H), 2.39 (s, 3H) 1-233 CF₃ SCH₂CONMe₂ SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 8.46 (d, 1H), 8.09 (d, 1H), 4.05 (s, 2H), 4.80 (q, 2H), 3.90 (s, 3H), 3.85 (s, 3H), 2.38 (s, 3H), 1.12 (t, 3H) 1-234 CF₃ SCH₂COOH SO₂Me ¹H NMR, CD₃OD, 400 MHz 8.59 (d, 1H), 8.00 (d, 1H), 4.11 (s, 2H), 3.56 (s, 3H), 2.44 (s, 3H) 1-235 CF₃ SCH₂COOH SO₂Et ¹H NMR, CD₃OD, 400 MHz 8.50 (d, 1H), 7.94 (d, 1H), 4.10 (s, 2H), 3.81 (q, 2H), 2.40 (s, 3H), 1.22 (t, 3H) 1-236 Me SO₂—CH₂—CH₂—CH═CH₂ CF₃ ¹H NMR, CDCl₃, 400 MHz 9.13 (bs, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 5.79 (m, 1H), 5.11 (t, 2H), 3.30 (dd, 2H), 2.71 (s, 3H), 2.65 (m, 2H), 2.51 (s, 3H) 1-237 Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.58 (s, 1H), 8.02 (d, 1H), 7.77 (d, 1H), 4.42 (q, 2H), 2.73 (s, 3H), 2.39 (s, 3H), 1.12 (t, 3H) 1-238 CF₃ SEt SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.50 (d, 1H), 7.74 (d, 1H), 3.51 (s, 3H), 3.09 (q, 2H), 2.48 (s, 3H), 1.32 (t, 3H) 1-239 OMe NO2 Cl ¹H NMR, DMSO-d₆, 400 MHz 11.48 (s, 1H), 7.91 (d, 1H), 7.69 (d, 1H), 4.91 (s, 3H), 2.48 (s, 3H) 1-240 OMe NH(CO)i-Pr Cl ¹H NMR, DMSO-d₆, 400 MHz 11.10 (s, 1H), 9.54 (s, 1H), 7.59 (d, 1H), 7.42 (d, 1H), 3.78 (s, 3H), 2.68 (m, 1H), 2.38 (s, 3H), 1.13 (d, 6H) 1-241 OMe NH(CO)CH₂Ph Cl ¹H NMR, DMSO-d₆, 400 MHz 11.08 (s, 1H), 9.91 (s, 1H), 7.59 (d, 1H), 7.46-7.29 (m, 5H), 3.67 (s, 3H), 2.35 (s, 3H) 1-242 CF₃ SEt SO₂Et ¹H NMR, CD₃OD, 400 MHz 8.55 (d, 1H), 7.96 (d, 1H), 3.81 (q, 2H), 3.11 (q, 2H), 2.45 (s, 3H), 1.31 (t, 3H), 1.24 (t, 3H) 1-243 CF₃ S(O)Et SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 8.49 (bs, 1H), 8.22 (d, 1H), 3.54 (s, 3H), 3.25-3.40 (m, 2H), 2.38 (s, 3H), 1.40 (t, 3H) 1-244 Cl Me Cl ¹H NMR, DMSO-d₆, 400 MHz 11.41 (s, 1H), 7.62 (d, 1H), 7.54 (d, 1H), 2.38 (s, 3H) 1-245 Me 3,5-dimethyl- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz pyrazol-1-yl 11.54 (s, 1H), 8.09 (d, 1H), 7.98 (d, 1H), 3.17 (s, 3H), 2.39 (s, 3H), 2.21 (s, 3H), 1.98 (s, 3H), 1.82 (s, 3H) 1-247 Me 1,2,3-triazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.60 (s, 1H), 8.53 (s, 1H), 8.17 (d, 1H), 8.11 (d, 1H), 8.04 (s, 1H), 3.12 (s, 3H), 2.39 (s, 3H), 1.90 (s, 1H) 1-248 Me Me SMe ¹H NMR, DMSO-d₆, 400 MHz 11.08 (s, 1H), 7.41 (d, 1H), 7.18 (d, 1H), 2.36 (s, 3H), 2.31 (s, 3H), 2.25 (s, 3H) 1-249 Me pyrrolidin-2-on-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.49 (s, 1H), 8.00 (d, 1H), 7.86 (d, 1H), 3.78-3.60 (m, 2H), 3.19 (s, 3H), 2.27 (s, 3H) 1-250 CF₃ S(O)Et SO₂Et ¹H NMR, CD₃OD, 400 MHz 8.56 (bs, 1H), 8.13 (d, 1H), 3.60-3.70 (m, 4H), 2.45 (s, 3H), 1.53 (t, 3H), 1.32 (t, 3H) 1-251 Cl pyrazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.72 (s, 1H), 8.24 (d, 1H), 8.17 (d, 1H), 8.04 (d, 1H), 7.88 (d, 1H), 3.18 (s, 3H), 2.39 (s, 3H) 1-252 Me 3-methylpyrazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.51 (s, 1H), 8.08 (d, 1H), 7.98 (d, 1H), 7.81 (d, 1H), 6.38 (d, 1H), 3.06 (s, 3H), 2.40 (s, 3H) 1-253 Cl CH₂—N(Et)OMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.62 (s, 1H), 8.14 (d, 1H), 7.91 (d, 1H), 4.53 (s, 2H), 3.57 (s, 3H), 3.14 (s, 3H), 2.87 (q, 2H), 2.40 (s, 3H), 1.13 (t, 3H) 1-254 Me Me Cl ¹H NMR, DMSO-d₆, 400 MHz 11.18 (s, 1H), 7.43 (d, 1H), 7.39 (d, 1H), 2.38 (s, 3H), 2.37 (s, 3H), 2.35 (s, 3H) 1-255 OH Cl Cl ¹H NMR, DMSO-d₆, 400 MHz 7.68 (d, 1H), 7.39 (d, 1H), 2.36 (s, 3H) 1-256 Me 1,2,4-triazol-1-yl SO₂Me 1-257 Me 4-methoxypyrazol-1- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz yl 11.54 (s, 1H), 8.08 (d, 1H), 7.99 (d, 1H), 7.74 (s, 1H), 7.66 (s, 1H), 3.75 (s, 3H), 3.11 (s, 3H), 2.39 (s, 3H) 1-258 Me 1,2,4-triazol-1-y1 CF₃ 1-259 Me tetrahydro- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz pyrimidin-2-(1H)-on- 11.51 (s, 1H), 7.95 (d, 1H), 7.77 (d, 1H), 1-yl 3.19 (s, 3H), 2.90 (s, 3H), 2.40 (s, 3H), 2.26 (s, 3H) 1-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.36 (s, 1H), 7.76 (d, 1H), 7.30 (d, 1H), 5.60 (t, 1H), 4.25 (t, 2H), 3.41 (m, 2H), 2.40 (s, 3H), 1.05 (t, 3H) 1-261 Me NH—iPr SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.36 (s, 1H), 7.78 (d, 1H), 7.20 (d, 1H), 5.58 (d, 1H), 3.69 (m, 1H), 3.28 (s, 3H), 2.40 (s, 3H), 1.14 (d, 6H) 1-262 Cl NH—CH₂—(CO)NHEt Cl ¹H NMR, DMSO-d₆, 400 MHz 11.38 (s, 1H), 8.08 (t, 1H), 7.47 (d, 1H), 7.08 (d, 1H), 5.69 (t, 1H), 3.97 (d, 2H), 3.15 (m, 2H), 2.38 (s, 3H), 1.04 (t, 3H) 1-263 Me NH—CH₂—(CO)NMe₂ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1H), 7.70 (d, 1H), 7.20 (d, 1H), 6.41 (t, 1H), 4.10 (d, 2H), 3.25 (s, 3H), 1-264 Me NH—CH₂-furan-2-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 13.39 (bs, 1H), 11.30 (s, 1H), 7.66 (d, 1H), 7.32 (d, 1H), 5.60 (broad, 1H), 4.07-3.98 (m, 1H), 3.84-3.77 (m, 1H), 3.72-3.64 (m, 1H), 2.38 (s, 3H), 2.03-1.92 (m, 1H), 1.90-1.79 (m, 2H), 1.63-1.54 (m, 1H). 1-265 Me NH—CH₂—(CO)NHEt SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1H), 8.12 (broad, 1H), 7.72 (d, 1H), 7.22 (d, 1H), 6.18 (t, 1H), 3.87 (d, 2H), 2.39 (s, 3H), 1.02 (t, 3H), 1-266 Me F SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.49 (s, 1H), 7.83 (t, 1H), 7.67 (d, 1H), 3.38 (s, 3H) 1-267 F SO₂Me SO₂Me 1-268 Cl (4-cyclopropyl-3- Cl ¹H NMR, DMSO-d₆, 400 MHz methyl-5-oxo-4,5- 11.50 (s, 1H), 7.69 (d, 1H), 7.65 (d, 1H), dihydro-1H-1,2,4- 5.06 (s, 2H), 2.79 (m, 1H), 2.38 (s, 3H), triazol-1-yl)methyl 2.14 (s, 3H) 1-269 Cl [4-methyl-5-oxo-3- Cl ¹H NMR, DMSO-d₆, 400 MHz (2,2,2-trifluoro- 11.50 (s, 1H), 7.70 (d, 1H), 7.68 (d, 1H), ethoxy)-4,5-dihydro- 5.12 (s, 2H), 4.85 (q, 2H), 3.07 (s, 3H), 1H-1,2,4-triazol-1- 2.38 (s, 3H) yl]methyl 1-270 Cl (3-isopropoxy-4- Cl ¹H NMR, DMSO-d₆, 400 MHz methyl-5-oxo-4,5- 11.50 (s, 1H), 7.69 (d, 1H), 7.65 (d, 1H), dihydro-1H-1,2,4- 5.08 (s, 2H), 4.72 (m, 1H), 2.98 (m, 1H), triazol-1-yl]methyl 2.38 (s, 3H), 1.27 (d, 6H) 1-271 Cl (4-methyl-5-oxo-4,5- Cl ¹H NMR, DMSO-d₆, 400 MHz dihydro-1H-1,2,4- 11.51 (s, 1H), 7.86 (s, 1H), 7.70 (d, 1H), triazol-1-yl)methyl 7.66 (d, 1H), 5.14 (s, 2H), 3.18 (m, 1H), 2.38 (s, 3H). 1-272 Me Cl SO₂Et 1-273 SO₂Me F Cl ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 8.14 (t, 1H), 7.63 (d, 1H), 3.45 (s, 3H), 2.41 (s, 3H) 1-274 Me 1,2,3-triazol-1-yl SO₂Me 1-275 Me isobutyl(methyl)- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz carbamoylamino 11.49 (s, 1H), 8.01 (s, 1H), 7.89 (d, 1H), 7.69 (d, 1H), 3.16 (bs, 5H), 2.98 (s, 3H), 2.39 (s, 3H), 2.21 (s, 3H), 1.95 (m, 1H), 0.87 (d, 6H) 1-276 Me 3-oxomorpholin-4-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.54 (s, 1H), 8.03 (d, 1H), 7.88 (d, 1H), 4.32 (q, 2H), 4.05-3.89 (m, 2H), 3.70-3.66 (m, 1H), 3.60-3.57 (m, 1H), 3.33 (s, 3H), 2.49 (s, 3H), 2.30 (s, 3H) 1-277 OMe [ethyl(methyl- Cl ¹H NMR, DMSO-d₆, 400 MHz sulfonyl)amino]- 11.21 (s, 1H), 7.66 (d, 1H), 7.43 (d, 1H), methyl 4.52 (s, 2H), 3.85 (s, 3H), 3.10 (q, 2H), 3.01 (s, 3H), 2.39 (s, 3H), 0.98 (t, 3H) 1-278 F SO₂Me CF₃ 1-279 OMe benzoylamino Cl ¹H NMR, DMSO-d₆, 400 MHz 11.15 (s, 1H), 10.16 (s, 1H), 8.03 (d, 2H), 7.68-7.49 (m, 5H), 3.82 (s, 3H), 2.38 (s, 3H) 1-280 OMe cyclopropylcarbonyl- Cl ¹H NMR, DMSO-d₆, 400 MHz amino 11.10 (s, 1H), 10.88 (s, 1H), 7.59 (d, 1H), 7.41 (d, 1H), 3.78 (s, 3H), 2.38 (s, 3H), 1.89 (broad, 1H), 0.79 (m, 4H) 1-281 OMe propionylamino Cl ¹H NMR, DMSO-d₆, 400 MHz 11.08 (s, 1H), 9.59 (s, 1H), 7.59 (d, 1H), 7.43 (d, 1H), 3.78 (s, 3H), 2.38 (m, 4H), 1.13 (m, 4H) 1-282 NO₂ SO₂Me SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.75 (s, 1H), 8.6 (d, 1H), 8.15 (d, 1H), 3.68 (s, 3H), 3.58 (s, 3H), 2.45 (s, 3H) 1-283 NO₂ SO₂Me Cl ¹H NMR, DMSO-d₆, 400 MHz 11.9 (s, 1H), 8.32 (d, 1H), 8.22 (d, 1H), 3.58 (s, 3H), 2.35 (s, 3H) 1-284 NO₂ SOMe SO₂Me ¹H NMR, MeOD, 400 MHz 8.5 (d, 1H), 8.22 (d, 1H), 3.55 (s, 3H), 2.6 (s, 3H), 2.38 (s, 3H) 1-285 NO₂ SOMe Br ¹H NMR, CDCl₃, 400 MHz 7.88 (d, 1H), 7.72 (d, 1H), 3.22 (s, 3H), 2.43 (s, 3H) 1-286 NO₂ SOMe Cl ¹H NMR, DMSO-d₆, 400 MHz 11.89 (s, 1H), 8.15 (d, 1H), 8.05 (d, 1H), 3.19 (s, 3H), 2.35 (s, 3H) 1-287 NO₂ SMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.9 (s, 1H), 8.45 (d, 1H), 8.38 (d, 1H), 3.61 (s, 3H), 2.52 (s, 3H), 2.32 (s, 3H) 1-288 NO₂ SMe Br ¹H NMR, CDCl₃, 400 MHz 8.18 (s, 1H), 7.96 (d, 1H), 7.65 (d, 1H), 2.48 (s, 3H), 2.4 (s, 3H) 1-289 NO₂ SMe Cl ¹H NMR, CDCl₃, 400 MHz 8.3 (s, 1H), 7.76 (d, 1H), 7.72 (d, 1H), 2.49 (s, 3H), 2.42 (s, 3H) 1-290 Cl CH₂OCH(CH₃)₂ SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.55 (s, 1H), 7.98 (d, 1H), 7.71 (d, 1H), 5.03 (s, 2H), 3.82 (m, 1H), 3.42 (q, 2H), 2.52 (s, 3H), 1.25 (d + t, 9H) 1-291 Cl CH₂OEt SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.58 (s, 1H), 7.96 (d, 1H), 7.71 (d, 1H), 5.05 (s, 2H), 3.69 (m, 2H), 3.4 (q, 2H), 2.52 (s, 3H), 1.25 (t, 6H) 1-292 Cl CH₂OMe SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.55 (s, 1H), 7.98 (d, 1H), 7.72 (d, 1H), 5.02 (s, 2H), 3.5 (s, 3H), 3.36 (q, 2H), 2.52 (s, 3H), 1.25 (t, 3H) 1-293 Cl CH₂OCH₂C₂F₅ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.38 (s, 1H), 8.09 (d, 1H), 7.8 (d, 1H), 5.32 (s, 2H), 4.12 (t, 2H), 3.2 (s, 3H), 2.52 (s, 3H) 1-294 Cl CH₂OCH₂CHF₂ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.15 (d, 1H), 8.14 (s, 1H), 7.8 (d, 1H), 5.94 (tt, 1H), 5.3 (s, 2H), 3.9 (dt, 2H), 3.25 (s, 3H), 2.52 (s, 3H) 1-295 Cl CH₂OCH₂CCH SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.42 (s, 1H), 8.02 (d, 1H), 7.75 (d, 1H), 5.19 (s, 2H), 4.32 (d, 2H), 3.4 (q, 2H), 2.55 (t, 1H), 2.52 (s, 3H), 1.28 (t, 3H) 1-296 Cl CH₂OC₂H₄OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.42 (s, 1H), 8.08 (d, 1H), 7.73 (d, 1H), 5.18 (s, 2H), 3.8 (dd, 2H), 3.58 (dd, 2H), 3.32 (s, 3H), 3.3 (s, 3H), 2.52 (s, 3H) 1-297 Cl CH₂(OC₂H₄)₂OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.78 (s, 1H), 8.09 (d, 1H), 7.72 (d, 1H), 5.18 (s, 2H), 3.82 (dd, 2H), 3.66 (dd, 2H), 3.58 (dd, 2H), 3.48 (dd, 2H), 3.31 (s, 3H), 3.29 (s, 3H), 2.51 (s, 3H) 1-298 Cl 5-ethoxymethyl-4,5- SO₂Et ¹H NMR, CDCl₃, 400 MHz dihydro-1,2-oxazol- 8.43 (s, 1H), 8.09 (d, 1H), 7.9 (d, 1H), 3-yl 5.05 (m, 1H), 3.72 (dd, 1H), 3.62 (dd, 1H), 3.6 (q, 2H), 3.46 (dd, 1H), 3.38 (q, 2H), 3.26 (dd, 1H), 2.5 (s, 3H), 1.28 (t, 3H), 1.22 (t, 3H) 1-299 Cl 5-methoxymethyl- SO₂Et ¹H NMR, CDCl₃, 400 MHz 4,5-dihydro-1,2- 8.42 (s, 1H), 8.09 (d, 1H), 7.9 (d, 1H), oxazol-3-yl 5.05 (m, 1H), 3.69 (dd, 1H), 3.58 (dd, 1H), 3.45 (dd, 1H), 3.45 (s, 3H), 3.38 (q, 2H), 3.22 (dd, 1H), 2.5 (s, 3H), 1.28 (t, 3H) 1-300 Et SOMe CF₃ ¹H NMR, CDCl₃, 400 MHz 9.52 (s, 1H), 7.68 (s, 2H), 3.43 (m, 1H), 3.35 (m, 1H), 3.0 (s, 3H), 2.5 (s, 3H), 1.2 (t, 3H) 1-301 iPr SMe CF₃ ¹H NMR, CDCl₃, 400 MHz 7.88 (s, 1H), 7.7 (d, 1H), 7.51 (d, 1H), 4.32 (m, 1H), 2.52 (s, 3H), 2.32 (s, 3H), 1.45 (d, 6H) 1-302 Et SMe CF₃ ¹H NMR, CDCl₃, 400 MHz 7.82 (s, 1H), 7.71 (d, 1H), 7.59 (d, 1H), 3.22 (q, 2H), 2.51 (s, 3H), 2.35 (s, 3H), 1.3 (t, 3H) 1-303 Et SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.38 (s, 1H), 7.88 (d, 1H), 7.8 (d, 1H), 3.32 (q, 2H), 3.28 (s, 3H), 2.5 (s, 3H), 1.32 (t, 3H) 1-304 cPr SOMe CF₃ ¹H NMR, CDCl₃, 400 MHz 9.92 (s, 1H), 7.7 (m, 2H), 3.15 (s, 3H), 2.82 (m, 1H), 2.52 (s, 3H), 1.2 (m, 1H), 1.1 (m, 1H), 0.98 (m, 1H), 0.7 (m, 1H) 1-305 CH═CH₂ SMe CF₃ ¹H NMR, CDCl₃, 400 MHz 7.78 (m, 1H), 7.68 (d, 1H), 7.68 (s, 1H), 7.4 (dd, 1H), 5.7 (d, 1H), 5.6 (d, 1H), 2.48 (s, 3H), 2.29 (s, 3H) 1-306 Et SMe Cl ¹H NMR, CDCl₃, 400 MHz 7.82 (s, 1H), 7.45 (d, 1H), 7.4 (d, 1H), 3.18 (q, 2H), 2.5 (s, 3H), 2.42 (s, 3H), 1.25 (t, 3H) 1-307 Et SO₂Me Cl ¹H NMR, CDCl₃, 400 MHz 8.53 (s, 1H), 7.6 (d, 1H), 7.5 (d, 1H), 3.3 (s, 3H), 3.3 (q, 2H), 2.5 (s, 3H), 1.3 (t, 3H) 1-308 Cl NMe₂ Cl ¹H NMR, CDCl₃, 400 MHz 8.17 (bs, 1H), 7.45 (d, 1H), 7.40 (d, 1H), 2.92 (s, 6H), 2.49 (s, 3H) 1-309 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 7.94 (d, 1H), 7.40 (d, 1H), 4.63 (s, 2H), 3.76 (m, 2H), 3.58-3.45 (m, 6H), 3.37 (s, 3H), 3.18 (s, 3H), 3.10 (s, 3H), 2.46 (s, 3H), 1.95 (quin, 2H) 1-313 Me SO₂(CH₂)₂OMe CF₃ ¹H NMR, CDCl₃, 400 MHz 7.85 (d, 1H), 7.77 (d, 1H), 3.90 (t, 2H), 3.52 (t, 2H), 3.27 (s, 3H), 2.78 (s, 3H), 2.51 (s, 3H) 1-314 Me SOEt SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.07 (d, 1H), 7.73 (d, 1H), 3.47 (m, 1H), 3.33 (s, 3H), 3.22 (m, 1H), 2.87 (s, 3H), 2.51 (s, 3H), 1.52 (t, 3H) 1-315 Me SO₂Et SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.36 (d, 1H), 7.83 (d, 1H), 3.66 (q, 2H), 3.56 (s, 3H), 2.85 (s, 3H), 2.52 (s, 3H), 1.53 (t, 3H) 1-316 Me SMe 1,2,4- ¹H NMR, CDCl₃, 400 MHz triazol-1- 8.58 (s, 1H), 8.13 (s, 1H), 7.62 (d, 1H), yl 7.48 (d, 1H), 2.78 (s, 3H), 2.52 (s, 3H), 2.03 (s, 3H) 1-317 OEt SMe CF₃ ¹H NMR, CDCl₃, 400 MHz 8.21 (d, 1H), 7.65 (d, 1H), 4.38 (q, 2H), 2.48 (s + s, 6H), 1.59 (t, 3H) 1-318 Me S(CH₂)₂OMe CF₃ ¹H NMR, CDCl₃, 400 MHz 7.71 (d, 1H), 7.57 (d, 1H), 3.55 (t, 2H), 3.32 (s, 3H), 2.92 (t, 2H), 2.79 (s, 3H), 2.51 (s, 3H) 1-319 Me SOMe 1,2,4- ¹H NMR, CDCl₃, 400 MHz triazol-1- 8.41 (s, 1H), 8.10 (s, 1H), 7.71 (d, 1H), yl 7.35 (d, 1H), 3.13 (s, 3H), 2.87 (s, 3H), 2.51 (s, 3H) 1-320 OEt SOMe CF₃ ¹H NMR, CDCl₃, 400 MHz 8.32 (d, 1H), 7.72 (d, 1H), 4.64 (m, 1H), 4.13 (m, 1H), 3.13 (s, 3H), 2.50 (s, 3H), 1.61 (t, 3H) 1-321 Me SO(CH₂)₂OMe CF₃ ¹H NMR, CDCl₃, 400 MHz 7.68 (d, 1H), 7.63 (d, 1H), 3.87 (dt, 1H), 3.73 (m, 1H), 3.49 (dt, 1H), 3.35 (s, 3H), 3.03 (m, 1H), 2.77 (s, 3H), 2.49 (s, 3H) 1-322 Me SCH₂CCMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.06 (d, 1H), 7.66 (d, 1H), 3.61 (m, 2H), 3.44 (s, 3H), 2.81 (s, 3H), 2.52 (s, 3H), 1.73 (m, 3H) 1-323 Me S—c-Pen SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.11 (d, 1H), 7.63 (d, 1H), 3.63 (m, 1H), 3.42 (s, 3H), 2.77 (s, 3H), 2.51 (s, 3H), 1.98-1.90 (m, 2H), 1.85-1.73 (m, 2H), 1.63-1.55 (m, 4H) 1-324 OMe SMe OMe ¹H NMR, CDCl₃, 400 MHz 8.17 (d, 1H), 6.87 (d, 1H), 4.07 (s, 3H), 3.98 (s, 3H), 2.47 (s, 3H), 2.43 (s, 3H) 1-325 Me SCH₂CH═CHCH₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 7.94 (d, 1H), 7.61 (d, 1H), 5.68-5.45 (m, 2H), 3.58-3.42 (m, 5H), 2.73 (s, 3H), 2.51 (s, 3H), 1.63 (d, 3H) 1-326 Me SOCH₂CCMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.11 (m, 2H), 7.76 (d, 1H), 4.28-4.03 (m, 2H), 3.34 (s, 3H), 2.91 (s, 3H), 2.51 (s, 3H), 1.86 (t, 3H) 1-327 Me SO₂—c-Pen SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.40 (d, 1H), 7.83 (d, 1H), 4.45 (quin, 1H), 3.51 (s, 3H), 2.91 (s, 3H), 2.52 (s, 3H), 2.18 (m, 2H), 2.01 (m, 2H), 1.88 (m, 2H), 1.71 (m, 2H) 1-328 Me SO—c-Pen SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.11 (d, 1H), 7.74 (d, 1H), 3.98 (m, 1H), 3.33 (s, 3H), 2.88 (s, 3H), 2.51 (s, 3H), 2.28 (m, 1H), 2.05 (m, 1H), 1.91-1.51 (m, 6H) 1-329 Me S(CH₂)₃Cl SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.06 (d, 1H), 7.66 (d, 1H), 3.66 (t, 2H), 3.42 (s, 3H), 3.02 (t, 2H), 2.79 (s, 3H), 2.52 (s, 3H), 2.12 (quin, 2H) 1-330 Me SCH₂(4-F—Ph) SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.03 (d, 1H), 7.66 (d, 1H), 7.16 (m, 2H), 6.97 (m, 2H), 4.01 (s, 2H), 3.33 (s, 3H), 2.62 (s, 3H), 2.51 (s, 3H) 1-331 Me SO₂CH₂CCMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.36 (d, 1H), 7.87 (d, 1H), 4.60 (m, 2H), 3.51 (s, 3H), 2.98 (s, 3H), 2.52 (s, 3H), 1.83 (t, 3H) 1-332 Me SO₂CH₂CH═CHCH₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.35 (d, 1H), 7.83 (d, 1H), 5.93 (m, 1H), 5.61 (m, 1H), 4.34 (d, 2H), 3.54 (s, 3H), 2.83 (s, 3H), 2.51 (s, 3H), 1.77 (d, 3H) 1-333 Me SOCH₂CH═CHCH₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.02 (m, 1H), 7.73 (m, 1H), 6.07-5.87 (m, 1H), 5.75-5.60 (m, 1H), 4.10-3.83 (m, 2H), 3.32 (s, 3H), 2.86 (s, 3H), 2.51 (s, 3H), 1.78 (d, 3H) 1-334 Me SOCH₂-epoxy-Me SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.08 (m, 1H), 7.76 (d, 1H), 3.88-2.84 (m, 10H), 2.51 (s, 3H), 1.37 (m, 3H) 1-335 Me SO₂(CH₂)₃Cl SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.28 (d, 1H), 7.86 (d, 1H), 3.81-3.73 (m, 4H), 3.55 (s, 3H), 2.85 (s, 3H), 2.52 (m, 5H) 1-336 Me SO(CH₂)₃Cl SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.05 (d, 1H), 7.76 (d, 1H), 3.81-3.61 (m, 3H), 3.40-3.27 (m, 4H), 2.89 (s, 3H), 2.52 (s, 3H), 2.43 (m, 2H) 1-337 Me SOCH₂(4-F—Ph) SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 8.05 (d, 1H), 7.95 (d, 1H), 7.46 (dd, 2H), 7.27 (t, 2H), 4.70 (d, 1H), 4.41 (d, 1H), 3.47 (s, 3H), 2.81 (s, 3H), 2.41 (s, 3H) 1-338 Me SO₂CH₂(4-F—Ph) SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.42 (d, 1H), 7.85 (m, 1H), 7.69 (m, 1H), 7.40 (t, 2H), 7.07 (t, 2H), 4.93 (s, 2H), 3.59 (s, 3H), 2.49 (s, 3H), 2.43 (s, 3H) 1-339 Me SO₂Me C₂F₅ ¹H NMR, CDCl₃, 400 MHz 7.91-7.75 (m, 3H), 3.30 (s, 3H), 2.88 (s, 3H), 2.52 (s, 3H) 1-340 O(CH₂)₂OMe SMe CF₃ ¹H NMR, CDCl₃, 400 MHz 8.32 (d, 1H), 7.66 (d, 1H), 4.55 (m, 2H), 3.78 (m, 2H), 3.34 (s, 3H), 2.48 (s, 3H), 2.44 (s, 3H) 1-341 O(CH₂)₂OMe SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.56 (d, 1H), 7.91 (d, 1H), 4.47 (m, 2H), 3.79 (m, 2H), 3.43 (s, 3H), 3.31 (s, 3H), 2.45 (s, 3H) 1-342 O(CH₂)₂OMe SOMe CF₃ ¹H NMR, CDCl₃, 400 MHz 8.49 (d, 1H), 7.73 (d, 1H), 4.91 (dt, 1H), 4.21 (dt, 1H), 3.97 (dt, 1H), 3.60 (dt, 1H), 3.29 (s, 3H), 3.15 (s, 3H), 2.45 (s, 3H) 1-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 7.91 (d, 1H), 7.63 (d, 1H), 3.89-3.80 (m, 4H), 3.43 (s, 3H), 3.08 (m, 2H), 2.76 (s, 3H), 2.52 (s, 3H) 1-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.06 (d, 1H), 7.75 (d, 1H), 4.23 (m, 1H), 4.13 (m, 1H), 3.93 (q, 2H), 3.68 (m, 1H), 3.50 (m, 1H), 3.36 (s, 3H), 2.84 (s, 3H), 2.52 (s, 3H) 1-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.37 (d, 1H), 7.91-7.83 (m, 2H), 4.24 (t, 2H), 3.96 (t, 2H), 3.85 (q, 2H), 3.55 (s, 3H), 2.87 (s, 3H), 2.52 (s, 3H) 1-346 OEt SEt CF₃ ¹H NMR, CDCl₃, 400 MHz 8.22 (d, 1H), 7.66 (d, 1H), 4.37 (q, 2H), 3.03 (q, 2H), 2.50 (s, 3H), 1.59 (t, 3H), 1.22 (t, 3H) 1-347 O—CH₂—c-Pr SMe CF₃ ¹H NMR, CDCl₃, 400 MHz 8.22 (d, 1H), 7.65 (d, 1H), 4.19 (d, 2H), 2.51 (s, 3H), 2.49 (s, 3H), 1.38 (m, 1H), 0.71 (m, 2H), 0.40 (m, 2H) 1-348 OMe SEt CF₃ ¹H NMR, CDCl₃, 400 MHz 8.23 (d, 1H), 7.68 (d, 1H), 4.15 (s, 3H), 3.01 (q, 2H), 2.50 (s, 3H), 1.22 (t, 3H) 1-349 OMe SO₂Et CF₃ ¹H NMR, CDCl₃, 400 MHz 8.37 (d, 1H), 7.92 (d, 1H), 4.16 (s, 3H), 3.55 (q, 2H), 2.52 (s, 3H), 1.37 (t, 3H) 1-350 OMe SOEt CF₃ ¹H NMR, CDCl₃, 400 MHz 8.33 (d, 1H), 7.74 (d, 1H), 4.19 (s, 3H), 3.64 (m, 1H), 3.23 (m, 1H), 2.51 (s, 3H), 1.34 (t, 3H) 1-351 OEt SO₂Et CF₃ ¹H NMR, CDCl₃, 400 MHz 8.37 (d, 1H), 7.91 (d, 1H), 4.34 (q, 2H), 3.58 (q, 2H), 2.51 (s, 3H), 1.61 (t, 3H), 1.36 (t, 3H) 1-352 OEt SOEt CF₃ ¹H NMR, CDCl₃, 400 MHz 8.33 (d, 1H), 7.74 (d, 1H), 4.63 (quin, 1H), 4.13 (quin, 1H), 3.65 (m, 1H), 3.25 (m, 1H), 2.51 (s, 3H), 1.59 (t, 3H), 1.33 (t, 3H) 1-353 O—CH2—c-Pr SOMe CF₃ ¹H NMR, CDCl₃, 400 MHz 8.32 (d, 1H), 7.73 (d, 1H), 4.50 (dd, 1H), 3.97 (dd, 1H), 3.19 (s, 3H), 2.50 (s, 3H), 1.47 (m, 1H), 0.66 (m, 2H), 0.56 (m, 1H), 0.37 (m, 1H) 1-354 O—CH2—c-Pr SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.39 (d, 1H), 7.88 (d, 1H), 4.16 (d, 2H), 3.48 (s, 3H), 2.50 (s, 3H), 1.48 (m, 1H), 0.72 (m, 2H), 0.51 (m, 2H) 1-355 Me SEt SO₂Me ¹H NMR, CDCl₃, 400 MHz 7.96 (d, 1H), 7.63 (d, 1H), 3.43 (s, 3H), 2.86 (q, 2H), 2.76 (s, 3H), 2.52 (s, 3H), 1.29 (t, 3H)

TABLE 2 Compounds of the general formula (I) according to the invention in which R is ethyl

No X Y Z Physical data 2-1  CF₃ OCH₂CON(Me)Et SO₂Me 2-2  CF₃ OCH₂CON(Me)Et SO₂Et 2-4  CF₃ 2-(1H-pyrazol-1-yl)- SO₂Me ethoxyl 2-5  CF₃ 2-(1H-pyrazol-1-yl)- SO₂Et ethoxyl 2-6  CF₃ tetrahydrofuran-2-yl- SO₂Me methoxy 2-7  CF₃ tetrahydrofuran-2-yl- SO₂Et methoxy 2-8  CF₃ OH SO₂Me 2-9  CF₃ OH SO₂Et 2-10  CF₃ SH SO₂Me 2-11  CF₃ SH SO₂Et 2-15  CF₃ SMe SO₂Me 2-16  CF₃ SMe SO₂Et 2-17  CF₃ S(O)Me SO₂Me 2-24  CF₃ S(O)Me SO₂Et 2-25  CF₃ S(O)₂Me SO₂Me 2-26  CF₃ S(O)₂Me SO₂Et 2-27  CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethoxy 2-28  CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethyl}sulfanyl 2-29  CF₃ 2-[(methylsulfonyl)- SO₂Et amino]ethyl}sulfanyl 2-30  NO₂ O(CH₂)₂OMe OMe 2-31  NO₂ OMe Me 2-32  NO₂ NH₂ OMe 2-33  NO₂ NH₂ SO₂Et 2-34  NO₂ NH₂ Cl 2-35  NO₂ NHMe Cl 2-36  NO₂ NMe₂ Cl 2-37  NO₂ NH₂ Br 2-38  NO₂ NHMe Br 2-39  NO₂ NMe₂ Br 2-40  NO₂ NH₂ F 2-41  NO₂ NHMe F 2-42  NO₂ NMe₂ F 2-43  NO₂ NH₂ SO₂Me 2-44  NO₂ NHMe SO₂Me 2-45  NO₂ NMe₂ SO₂Me 2-46  NO₂ NH₂ 1H-1,2,4- triazol-1- yl 2-47  NO₂ NHMe 1H-1,2,4- triazol-1- yl 2-48  NO₂ NMe₂ 1H-1,2,4- triazol-1- yl 2-49  Me F F ¹H NMR, DMSO-d₆, 400 MHz 11.26 (s, 1 H), 7.49 (m, 2 H), 2.8 (q, 2 H), 2.38 (s, 3 H), 1.25 (t, 3 H) 2-50  Me F Cl ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1 H), 7.61 (t, 1 H), 7.48 (d, 1 H), 2.79 (q, 2 H), 2.35 (s, 1 H), 1.26 (t, 3 H) 2-51  Me SMe CF₃ 2-52  Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.45 (s, 1 H), 8.05 (d, 1 H), 7.79 (d, 1 H), 3.44 (s, 3 H), 2.80 (q, 2 H), 2.48 (s, 3 H), 1.28 (t, 3 H) 2-53  Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1 H), 8.27 (d, 1 H), 8.08 (d, 1 H), 3.60 (s, 3 H), 3.58 (s, 3 H), 2.81 (q, 2 H), 2.71 (s, 3 H), 1.27 (t, 3 H) 2-54  Me SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.05 (bs, 1 H), 7.88 (d, 1 H), 7.78 (d, 1 H), 3.20 (s, 3 H), 2.90 (q, 2 H), 2.75 (s, 3 H), 1.40 (t, 3 H) 2-55  Me Cl CF₃ 2-56  Me S(O)Me CF₃ ¹H NMR, DMSO₆, 400 MHz 11.44 (s, 1 H), 7.88 (m, 2 H), 3.05 (s, 3 H), 2.87 (s, 3 H), 2.82 (q, 2 H), 1.28 (t, 3 H) 2-57  Me SEt OMe 2-58  Me NMe₂ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1 H), 7.88 (d, 1 H), 7.60 (d, 1 H), 3.31 (s, 3 H), 2.84 (s, 6 H), 2.80 (q, 2 H), 2.39 (s, 3 H), 1.28 (t, 3 H) 2-59  Me NH(CH₂)₂OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.84 (bs, 1 H), 7.52 (d, 1 H), 7.09 (d, 1 H), 5.68 (bs, 1 H), 3.57 (m, 2 H), 3.35 (m, 5 H), 3.13 (s, 3 H), 2.90 (q, 2 H), 2.37 (s, 3 H), 1.40 (t, 3 H) 2-60  Me O(CH₂)₄OMe SO₂Me 2-61  Me NH₂ SO₂Me 2-62  Me O(CH₂)₂—O(3,5-di- SO₂Me methoxypyrimidin-2-yl 2-63  Me O(CH₂)₂—O—NMe₂ Cl 2-64  Me O(CH₂)₂—NH(CO)NMe₂ Cl 2-65  Me O(CH₂)-5-pyrrolidin- Br 2-one 2-66  Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 2-67  Me O(CH₂)—(CO)NEt₂ Br 2-68  Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H-1,2,4- triazol-3-one 2-69  Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 2-70  Me O(CH₂)₂—NHCO₂Me Cl 2-71  Me 4,5-dihydro-1,2- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz oxazol-3-yl 11.46 (s, 1 H), 8.04 (d, 1 H), 7.90 (d, 1 H), 4.50 (t, 2 H), 3.35 (t, 2 H), 3.27 (s, 3 H), 2.82 (q, 2 H), 2.35 (s, 3 H), 1.27 (t, 3 H), 2-72  Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.34 (s, 1 H), 7.92 (d, 1 H), 7.59 (d, 1 H), 3.27 (s, 3 H), 2.80 (q, 2 H), 2.66 (s, 3 H), 2.36 (s, 3 H), 1.27 (t, 3 H) 2-73  Me OH SO₂Me 2-74  Me O—CH₂—NHSO₂cPr Cl 2-75  Me O(CH₂)₂NHSO2Me SO₂Me 2-76  Me S(O)Me SO₂Me 2-77  Me SMe SO₂Me 2-78  Me SMe OMe 2-79  Me S(O)Me OMe 2-80  Me SO₂Me OMe 2-81  Me SMe Cl 2-82  Me S(O)Me Cl 2-83  Me SO₂Me Cl 2-84  Me [1,4]dioxan-2-yl-methoxy SO₂Me 2-85  Me [1,4]dioxan-2-yl-methoxy SO₂Et 2-86  Me O(CH₂)₄OMe SO₂Et 2-87  Me O(CH₂)₃OMe SO₂Me 2-88  Me O(CH₂)₃OMe SO₂Et 2-89  Me O(CH₂)₂OMe SO₂Me 2-90  Me O(CH₂)₂OMe SO₂Et 2-91  Me S(O)Me SO₂Me 2-92  Me SMe SO₂Me 2-93  Me SMe OMe 2-94  Me S(O)Me OMe 2-95  Me SO₂Me OMe 2-96  Me SMe Cl 2-97  Me S(O)Me Cl 2-98  Me SO₂Me Cl 2-99  Me SMe Br 2-100 Me SOMe Br 2-101 Me SO₂Me Br 2-102 Me SMe I 2-103 Me SOMe I 2-104 Me SO₂Me I 2-105 Me SEt Cl 2-106 Me SOEt Cl 2-107 Me SO₂Et Cl 2-108 Me SEt Br 2-109 Me SOEt Br 2-110 Me SO₂Et Br 2-111 Me SEt I 2-112 Me SOEt I 2-113 Me SO₂Et I 2-114 Me SEt F 2-115 Me SOEt F 2-116 Me SO₂Et F 2-117 Cl OCH₂(CO)NMe₂ Cl ¹H NMR, DMSO-d₆, 400 MHz 11.44 (s, 1 H), 7.65 (d, 1 H), 7.49 (d, 1 H), 4.74 (s, 2 H), 3.02 (s, 3 H), 2.87 (s, 3 H), 2.81 (q, 2 H), 1.27 (t, 3 H) 2-118 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.60 (s, 1 H), 8.12 (d, 1 H), 7.98 (d, 1 H), 5.27 (s, 2 H), 4.30 (q, 2 H), 3.38 (s, 3 H), 2.83 (q, 2 H), 1.30 (t, 3 H) 2-119 Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz dihydro-1,2-oxazol-3-yl 11.62 (s, 1 H), 8.11 (m, 2 H), 5.20 (m, 1 H), 3.60 (m, 1 H), 3.44 (q, 2 H), 3.15 (m, 1 H), 3.02 (m, 2 H), 2.81 (q, 2 H), 1.28 (t, 3 H), 1.16 (t, 3 H) 2-120 Cl CH₂O-tetrahydro-furan-3-yl SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.70 (bs, 1 H), 7.94 (d, 1 H), 7.72 (d, 1 H), 5.06 (m, 2 H), 4.35 (m, 1 H), 3.73-3.92 (m, 4 H), 3.36 (q, 2 H), 2.92 (q, 2 H), 2.10 (m, 2 H), 1.40 (t, 3 H), 1.22 (t, 3 H) 2-121 Cl CH₂O-tetrahydrofuran-2-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.55 (s, 1 H), 8.14 (d, 1 H), 7.93 (d, 1 H), 3.58 (s, 3 H), 2.81 (q, 2 H), 2.48 (s, 3 H), 1.28 (t, 3 H) 2-122 Cl SMe SO₂Me 2-123 Cl F SMe 2-124 Cl CH₂OCH₂-tetrahydrofuran-2-yl SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.84 (bs, 1 H), 8.0 (d, 1 H), 7.70 (d, 1 H), 5.12 (s, 2 H), 4.05 (m, 1 H), 3.55-3.80 (m, 4 H), 3.28 (s, 3 H), 2.90 (q, 2 H), 1.78-2.0 (m, 3 H), 1.48-1.59 (m, 1 H), 1.40 (t, 3 H) 2-125 Cl CH₂OCH₂-tetrahydrofuran-3-yl SO₂Et 2-126 Cl O(CH₂)-5-pyrrolidin-2-one Cl 2-127 Cl SMe Cl ¹H NMR, DMSO-d₆, 400 MHz 11.41 (s, 1 H), 7.22 (d, 1 H), 7.68 (d, 1 H), 2.80 (q, 2 H), 2.43 (s, 3 H), 1.28 (t, 3 H) 2-128 Cl S(O)Me SO₂Me 2-129 Cl CH₂O-tetrahydrofuran-3-yl SO₂Et 2-130 Cl O(CH₂)₂OMe Cl 2-131 Cl O(CH₂)₂OMe SO₂Me 2-132 Cl O(CH₂)₄OMe SO₂Me 2-133 Cl O(CH₂)₄OMe SO₂Et 2-134 Cl O(CH₂)₃OMe SO₂Me 2-135 Cl O(CH₂)₃OMe SO₂Et 2-136 Cl O(CH₂)₂OMe SO₂Me 2-137 Cl O(CH₂)₂OMe SO₂Et 2-138 Cl [1,4]dioxan-2-yl-methoxy SO₂Me 2-139 Cl [1,4]dioxan-2-yl-methoxy SO₂Et 2-140 Cl SO₂Me Me 2-141 Cl SEt Me 2-142 Cl SOEt Me 2-143 Cl SO₂Et Me 2-144 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 2-145 Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.6 (s, 1 H), 8.16 (d, 1 H), 7.94 (d, 1 H), 3.49 (s, 3 H), 3.82 (q, 2 H), 1.28 (t, 3 H) 2-146 F SMe CF₃ 2-147 F S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.75 (bs, 1 H), 8.14 (dd, 1 H), 7.90 (d, 1 H), 2.81 (q, 2 H), 1.78-2.0 (m, 3 H), 1.28 (t, 3 H) 2-148 OMe OMe OMe 2-149 OMe SMe CF₃ 2-150 OMe S(O)Me CF₃ 2-151 OMe SO₂Me CF₃ 2-152 Et NH(CH₂)₂OMe SO₂Me 2-153 Et F SO₂Me 2-154 Et SMe CF₃ 2-155 CF₃ F SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.68 (s, 1 H), 8.3 (t, 1 H), 7.89 (d, 1 H), 3.49 (s, 3 H), 2.79 (q, 2 H), 1.27 (t, 3 H) 2-156 CF₃ F SO₂Et 2-157 CF₃ O(CH₂)₂OMe SO₂Et 2-158 CF₃ O(CH₂)₃OMe SO₂Et 2-159 CF₃ O(CH₂)₂OMe SO₂Me 2-160 CF₃ O(CH₂)₃OMe SO₂Me 2-161 CF₃ OCH₂CONMe₂ SO₂Me ¹H NMR, CD₃OD, 400 MHz 8.37 (d, 1 H), 7.74 (d, 1 H), 5.00 (s, 2 H), 3.43 (s, 3 H), 3.03 (s, 3 H), 2.95 (s, 3 H), 2.87 (q, 2 H), 1.38 (t, 3 H) 2-162 CF₃ OCH₂CONMe₂ SO₂Et 2-163 CF₃ OCH₂CONMe₂ Cl 2-164 CF₃ OCH₂CONMe₂ Br 2-165 CF₃ OCH₂CONMe₂ I 2-166 CF₃ OCH₂CONMe₂ F 2-167 CF₃ O(CH₂)₂OMe Cl 2-168 CF₃ O(CH₂)₃OMe Cl 2-169 CF₃ O(CH₂)₂OMe Br 2-170 CF₃ O(CH₂)₃OMe Br 2-171 CF₃ O(CH₂)₂OMe I 2-172 CF₃ O(CH₂)₃OMe I 2-173 CF₃ O(CH₂)₂OMe F 2-174 CF₃ O(CH₂)₃OMe F 2-175 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Me 2-176 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Et 2-177 CF₃ [1,4]dioxan-2-yl-methoxy Cl 2-178 CF₃ [1,4]dioxan-2-yl-methoxy Br 2-179 CF₃ [1,4]dioxan-2-yl-methoxy I 2-180 CF₃ [1,4]dioxan-2-yl-methoxy F 2-181 Br OMe Br 2-182 Br O(CH₂)₂OMe Br 2-183 Br O(CH₂)₂OMe SO₂Me 2-184 Br O(CH₂)₄OMe SO₂Et 2-185 Br O(CH₂)₃OMe SO₂Me 2-186 Br O(CH₂)₃OMe SO₂Et 2-187 Br O(CH₂)₂OMe SO₂Me 2-188 Br O(CH₂)₂OMe SO₂Et 2-189 Br [1,4]dioxan-2-yl-methoxy SO₂Me 2-190 Br [1,4]dioxan-2-yl-methoxy SO₂Et 2-191 Br SMe Me 2-192 Br SOMe Me 2-193 Br SO₂Me Me 2-194 Br SEt Me 2-195 Br SOEt Me 2-196 Br SO₂Et Me 2-197 I O(CH₂)₄OMe SO₂Me 2-198 I O(CH₂)₄OMe SO₂Et 2-199 I O(CH₂)₃OMe SO₂Me 2-200 I O(CH₂)₃OMe SO₂Et 2-201 I O(CH₂)₂OMe SO₂Me 2-202 I O(CH₂)₂OMe SO₂Et 2-203 I [1,4]dioxan-2-yl-methoxy SO₂Me 2-204 I [1,4]dioxan-2-yl-methoxy SO₂Et 2-205 I SMe Me 2-206 I SOMe Me 2-207 I SO₂Me Me 2-208 I SEt Me 2-209 I SOEt Me 2-210 I SO₂Et Me 2-211 CH₂SMe OMe SO₂Me 2-212 CH₂OMe OMe SO₂Me 2-213 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 2-214 CH₂O(CH₂)₂ NH(CH₂)₃OEt SO₂Me OMe 2-215 CH₂O(CH₂)₃ OMe SO₂Me OMe 2-216 CH₂O(CH₂)₂ NH(CH₂)₂OMe SO₂Me OMe 2-217 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 2-218 SO₂Me NH₂ CF₃ 2-219 SO₂Me F CF₃ 2-220 SO₂Me NHEt Cl 2-221 SMe SEt F 2-222 SMe SMe F 2-223 Me NH₂ Cl 2-224 Me NH₂ Br 2-225 Me NHMe Cl 2-226 Me NHMe Br 2-227 Me NMe₂ Cl 2-228 Me NMe₂ Br 2-227 Me NMe₂ Cl 2-228 Me NMe₂ Br 2-229 NO₂ O(CH₂)₂OMe Me 2-230 CF₃ S(O)₂Et SO₂Me 2-231 CF₃ S(O)₂Et SO₂Et 2-232 CF₃ SCH₂CONMe₂ SO₂Me 2-233 CF₃ SCH₂CONMe₂ SO₂Et 2-234 CF₃ SCH₂COOH SO₂Me 2-235 CF₃ SCH₂COOH SO₂Et 2-236 Me SO₂—CH₂—CH₂CH═CH₂ CF₃ 2-237 Cl Me SO₂Et 2-238 CF₃ SEt SO₂Me 2-239 OMe NO₂ Cl 2-240 OMe NH(CO)i-Pr Cl 2-241 OMe NH(CO)CH₂Ph Cl 2-242 CF₃ SEt SO₂Et 2-243 CF₃ S(O)Et SO₂Me 2-244 Cl Me Cl 2-245 Me 3,5-dimethylpyrazol-1-yl SO₂Me 2-247 Me 1,2,3-triazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.54 (s, 1 H), 8.22 (s, 2 H), 8.15 (d, 1 H), 8.08 (d, 1 H), 3.30 (s, 3 H), 2.81 (q, 2 H), 1.91 (s, 3 H), 1.27 (t, 3 H) 2-248 Me Me SMe 2-249 Me pyrrolidin-2-on-1-yl SO₂Me 2-250 CF₃ S(O)Et SO₂Et 2-251 Cl pyrazol-1-yl SO₂Me 2-252 Me 3-methylpyrazol-1-yl SO₂Me 2-253 Cl CH₂—N(Et)OMe SO₂Me 2-254 Me Me Cl 2-255 OH Cl Cl 2-256 Me 1,2,4-triazol-1-yl SO₂Me 2-257 Me 4-methoxypyrazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1 H), 8.08 (d, 1 H), 7.98 (d, 1 H), 7.74 (s, 1 H), 7.66 (s, 1 H), 3.75 (s, 3 H), 3.12 (s, 3 H), 2.81 (q, 2 H), 1.95 (s, 3 H), 1.27 (t, 3 H) 2-258 Me 1,2,4-triazol-1-yl CF₃ 2-259 Me tetrahydro- SO₂Me pyrimidin-2(1H)-on-1-yl 2-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me 2-261 Me NH—iPr SO₂Me 2-262 Cl NH—CH₂—(CO)NHEt Cl 2-263 Me NH—CH₂—(CO)NMe₂ SO₂Me 2-264 Me NH—CH₂-furan-2-yl SO₂Me 2-265 Me NH—CH₂—(CO)NHEt SO₂Me 2-266 Me F SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.46 (s, 1 H), 7.85 (t, 1 H), 7.66 (s, 1 H), 3.38 (s, 3 H), 2.81 (q, 2 H), 2.38 (s, 3 H), 1.27 (t, 3 H) 2-267 F SO₂Me SO₂Me 2-268 Cl (4-cyclopropyl-3- Cl methyl-5-oxo-4,5- dihydro-1H-1,2,4- triazol-1-yl)methyl 2-269 Cl [4-methyl-5-oxo-3- Cl (2,2,2-trifluoro- ethoxy)-4,5-dihydro- 1H-1,2,4-triazol-1- yl]methyl 2-270 Cl (3-isopropoxy-4- Cl methyl-5-oxo-4,5- dihydro-1H-1,2,4- triazol-1-yl]methyl 2-271 Cl (4-methyl-5-oxo-4,5- Cl dihydro-1H-1,2,4- triazol-1-yl)methyl 2-272 Me Cl SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.52 (s, 1 H), 8.02 (d, 1 H), 7.77 (d, 1 H), 3.41 (q, 2 H), 2.82 (q, 2 H), 2.75 (s, 3 H), 1.28 (t, 3 H), 1.14 (t, 3 H) 2-273 SO₂Me F Cl 2-274 Me 1,2,3-triazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.56 (s, 1 H), 8.55 (s, 1 H), 8.17 (d, 1 H), 8.08 (d, 1 H), 8.06 (s, 1 H), 3.14 (s, 3 H), 2.80 (q, 2 H), 1.91 (s, 3 H), 1.27 (t, 3 H) 2-275 Me isobutyl(methyl)- SO₂Me carbamoylamino 2-276 Me 3-oxomorpholin-4-yl SO₂Me 2-277 OMe [ethyl(methyl- Cl sulfonyl)amino]-methyl 2-278 F SO₂Me CF₃ 2-279 OMe benzoylamino Cl 2-280 OMe cyclopropylcarbonyl- Cl amino 2-281 OMe propionylamino Cl 2-282 NO₂ SO₂Me SO₂Me 2-283 NO₂ SO₂Me Cl 2-284 NO₂ SOMe SO₂Me 2-285 NO₂ SOMe Br 2-286 NO₂ SOMe Cl 2-287 NO₂ SMe SO₂Me 2-288 NO₂ SMe Br 2-289 NO₂ SMe Cl 2-290 Cl CH₂OCH(CH₃)₂ Br 2-291 Cl CH₂OEt SO₂Et 2-292 Cl CH₂OMe SO₂Et 2-293 Cl CH₂OCH₂C₂F₅ SO₂Me 2-294 Cl CH₂OCH₂CHF₂ SO₂Me 2-295 Cl CH₂OCH₂CCH SO₂Et 2-296 Cl CH₂OC₂H₄OMe SO₂Me 2-297 Cl CH₂(OC₂H₄)₂OMe SO₂Me 2-298 Cl 5-ethoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 2-299 Cl 5-methoxymethyl- SO₂Et 4,5-dihydro-1,2-oxazol- oxazol-3-yl 2-300 Et SOMe CF₃ 2-301 iPr SMe CF₃ 2-302 Et SMe CF₃ 2-303 Et SO₂Me CF₃ 2-304 cPr SOMe CF₃ 2-305 CH═CH₂ SMe CF₃ 2-306 Et SMe Cl 2-307 Et SO₂Me Cl 2-308 Cl NMe₂ Cl 2-309 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 2-313 Me SO₂(CH₂)₂OMe CF₃ 2-314 Me SOEt SO₂Me 2-315 Me SO₂Et SO₂Me 2-316 Me SMe 1,2,4- triazol-1- yl 2-317 OEt SMe CF₃ 2-318 Me S(CH₂)₂OMe CF₃ 2-319 Me SOMe 1,2,4- triazol-1- yl 2-320 OEt SOMe CF₃ 2-321 Me SO(CH₂)₂OMe CF₃ 2-322 Me SCH₂CCMe SO₂Me 2-323 Me S-c-Pen SO₂Me 2-324 OMe SMe OMe 2-325 Me SCH₂CH═CHCH₃ SO₂Me 2-326 Me SOCH₂CCMe SO₂Me 2-327 Me SO₂-c-Pen SO₂Me 2-328 Me SO-c-Pen SO₂Me 2-329 Me S(CH₂)₃Cl SO₂Me 2-330 Me SCH₂(4-F—Ph) SO₂Me 2-331 Me SO₂CH₂CCMe SO₂Me 2-332 Me SO₂CH₂CH═CHCH₃ SO₂Me 2-333 Me SOCH₂CH═CHCH₃ SO₂Me 2-334 Me SOCH₂-Epoxy-Me SO₂Me 2-335 Me SO₂(CH₂)₃Cl SO₂Me 2-336 Me SO(CH₂)₃Cl SO₂Me 2-337 Me SOCH₂(4-F—Ph) SO₂Me 2-338 Me SO₂CH₂(4-F—Ph) SO₂Me 2-339 Me SO₂Me C₂F₅ 2-340 O(CH₂)₂OMe SMe CF₃ 2-341 O(CH₂)₂OMe SO₂Me CF₃ 2-342 O(CH₂)₂OMe SOMe CF₃ 2-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me 2-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me 2-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me 2-346 OEt SEt CF₃ 2-347 O—CH₂-c-Pr SMe CF₃ 2-348 OMe SEt CF₃ 2-349 OMe SO₂Et CF₃ 2-350 OMe SOEt CF₃ 2-351 OEt SO₂Et CF₃ 2-352 OEt SOEt CF₃ 2-353 O—CH₂-c-Pr SOMe CF₃ 2-354 O—CH₂-c-Pr SO₂Me CF₃ 2-355 Me SEt SO₂Me

TABLE 3 Compounds of the general formula (I) according to the invention in which R is iso-propyl

No. X Y Z Physical data 3-1  CF₃ OCH₂CON(Me)Et SO₂Me 3-2  CF₃ OCH₂CON(Me)Et SO₂Et 3-4  CF₃ 2-(1H-pyrazol-1-yl)-ethoxyl SO₂Me 3-5  CF₃ 2-(1H-pyrazol-1-yl)-ethoxyl SO₂Et 3-6  CF₃ tetrahydrofuran-2-yl-methoxy SO₂Me 3-7  CF₃ tetrahydrofuran-2-yl-methoxy SO₂Et 3-8  CF₃ OH SO₂Me 3-9  CF₃ OH SO₂Et 3-10  CF₃ SH SO₂Me 3-11  CF₃ SH SO₂Et 3-15  CF₃ SMe SO₂Me 3-16  CF₃ SMe SO₂Et 3-17  CF₃ S(O)Me SO₂Me 3-24  CF₃ S(O)Me SO₂Et 3-25  CF₃ S(O)₂Me SO₂Me 3-26  CF₃ S(O)₂Me SO₂Et 3-27  CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethoxy 3-28  CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethyl}sulfanyl 3-29  CF₃ 2-[(methylsulfonyl)- SO₂Et amino]ethyl}sulfanyl 3-30  NO₂ O(CH₂)₂OMe OMe 3-31  NO₂ OMe Me 3-32  NO₂ NH₂ OMe 3-33  NO₂ NH₂ SO₂Et 3-34  NO₂ NH₂ Cl 3-35  NO₂ NHMe Cl 3-36  NO₂ NMe₂ Cl 3-37  NO₂ NH₂ Br 3-38  NO₂ NHMe Br 3-39  NO₂ NMe₂ Br 3-40  NO₂ NH₂ F 3-41  NO₂ NHMe F 3-42  NO₂ NMe₂ F 3-43  NO₂ NH₂ SO₂Me 3-44  NO₂ NHMe SO₂Me 3-45  NO₂ NMe₂ SO₂Me 3-46  NO₂ NH₂ 1H-1,2,4- triazol-1- yl 3-47  NO₂ NHMe 1H-1,2,4- triazol-1- yl 3-48  NO₂ NMe₂ 1H-1,2,4- triazol-1- yl 3-49  Me F F 3-50  Me F Cl 3-51  Me SMe CF₃ 3-52  Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.38 (s, 1 H), 8.06 (d, 1 H), 7.77 (d, 1 H), 3.44 (s, 3 H), 3.22 (m, 1 H), 2.48 (s, 3 H), 1.31 (d, 6 H) 3-53  Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.40 (s, 1 H), 8.29 (d, 1 H), 8.08 (d, 1 H), 3.60 (s, 3 H), 3.57 (s, 3 H), 3.21 (m, 1 H), 2.71 (s, 3 H), 1.31 (d, 6 H) 3-54  Me SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 7.91 (d, 1 H), 7.78 (d, 1 H), 3.26 (m, 4 H), 2.86 (s, 3 H), 1.41 (d, 6 H) 3-55  Me Cl CF₃ 3-56  Me S(O)Me CF₃ ¹H NMR, DMSO₆, 400 MHz 11.37 (s, 1 H), 7.89 (d, 1 H), 7.86 (d, 1 H), 3.25 (m, 1 H), 3.06 (s, 3 H), 2.86 (s, 3 H) 1.31 (d, 6 H) 3-57  Me SEt OMe 3-58  Me NMe₂ SO₂Me 3-59  Me NH(CH₂)₂OMe SO₂Me 3-60  Me O(CH₂)₄OMe SO₂Me 3-61  Me NH₂ SO₂Me 3-62  Me O(CH₂)₂—O(3,5-di- SO₂Me methoxypyrimidin-2-yl 3-63  Me O(CH₂)₂—O—NMe₂ Cl 3-64  Me O(CH₂)₂—NH(CO)NMe₂ Cl 3-65  Me O(CH₂)-5-pyrrolidin-2-one Br 3-66  Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 3-67  Me O(CH₂)—(CO)NEt₂ Br 3-68  Me O(CH₂)-5-2,4-dimethyl-2,4- Cl dihydro-3H-1,2,4-triazol-3-one 3-69  Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 3-70  Me O(CH₂)₂—NHCO₂Me Cl 3-71  Me 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 3-72  Me Me SO₂Me 3-73  Me OH SO₂Me 3-74  Me O—CH₂—NHSO₂cPr Cl 3-75  Me O(CH₂)₂NHSO2Me SO₂Me 3-76  Me S(O)Me SO₂Me 3-77  Me SMe SO₂Me 3-78  Me SMe OMe 3-79  Me S(O)Me OMe 3-80  Me SO₂Me OMe 3-81  Me SMe Cl 3-82  Me S(O)Me Cl 3-83  Me SO₂Me Cl 3-84  Me [1,4]dioxan-2-yl-methoxy SO₂Me 3-85  Me [1,4]dioxan-2-yl-methoxy SO₂Et 3-86  Me O(CH₂)₄OMe SO₂Et 3-87  Me O(CH₂)₃OMe SO₂Me 3-88  Me O(CH₂)₃OMe SO₂Et 3-89  Me O(CH₂)₂OMe SO₂Me 3-90  Me O(CH₂)₂OMe SO₂Et 3-91  Me S(O)Me SO₂Me 3-92  Me SMe SO₂Me 3-93  Me SMe OMe 3-94  Me S(O)Me OMe 3-95  Me SO₂Me OMe 3-96  Me SMe Cl 3-97  Me S(O)Me Cl 3-98  Me SO₂Me Cl 3-99  Me SMe Br 3-100 Me SOMe Br 3-101 Me SO₂Me Br 3-102 Me SMe I 3-103 Me SOMe I 3-104 Me SO₂Me I 3-105 Me SEt Cl 3-106 Me SOEt Cl 3-107 Me SO₂Et Cl 3-108 Me SEt Br 3-109 Me SOEt Br 3-110 Me SO₂Et Br 3-111 Me SEt I 3-112 Me SOEt I 3-113 Me SO₂Et I 3-114 Me SEt F 3-115 Me SOEt F 3-116 Me SO₂Et F 3-117 Cl OCH₂(CO)NMe₂ Cl ¹H NMR, DMSO-d₆, 400 MHz 11.37 (s, 1 H), 7.67 (d, 1 H), 7.48 (d, 1 H), 4.74 (s, 2 H), 3.25 (m, 1 H), 3.02 (s, 3 H), 2.87 (s, 3 H), 1.30 (d, 6 H) 3-118 Cl Cl SO₂Me 3-119 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.41 (bs, 1 H), 8.04 (d, 1 H), 7.77 (d, 1 H), 5.32 (s, 2 H), 4.05 (q, 2 H), 3.29 (m, 1 H), 3.20 (s, 3 H), 1.43 (d, 6 H) 3-120 Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, CDCl₃, 400 MHz dihydro-1,2-oxazol-3-yl 8.40 (bs, 1 H), 8.10 (d, 1 H), 7.94 (d, 1 H), 5.16 (m, 1 H), 3.72 (m, 1 H), 3.35 (q, 2 H), 3.25 (m, 2 H), 2.90 (m, 2 H), 1.42 (d, 6 H), 1.29 (t, 3 H) 3-121 Cl CH₂O-tetrahydrofuran-3-yl SO₂Me 3-122 Cl SMe SO₂Me 3-123 Cl SMe SO₂Me 3-124 Cl F SMe 3-125 Cl CH₂OCH₂-tetrahydrofuran-2-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.51 (s, 1 H), 8.11 (d, 1 H), 7.92 (d, 1 H), 5.1 (m, 2 H), 3.99 (m, 1 H), 3.71 (q, 1 H) 3.66-3.53 (m, 3 H), 3.39 (s, 3 H), 3.25 (q, 1 H), 1.93-1.71 (m, 3 H), 1.54 (m, 1 H), 1.31 (d, 6 H) 3-126 Cl CH₂OCH₂-tetrahydrofuran-3-yl SO₂Et 3-127 Cl O(CH₂)-5-pyrrolidin-2-one Cl 3-128 Cl SMe Cl 3-129 Cl S(O)Me SO₂Me 3-130 Cl CH₂O-tetrahydrofuran-3-yl SO₂Et 3-131 Cl O(CH₂)₂OMe Cl 3-132 Cl O(CH₂)₂OMe SO₂Me 3-133 Cl O(CH₂)₄OMe SO₂Me 3-134 Cl O(CH₂)₄OMe SO₂Et 3-135 Cl O(CH₂)₃OMe SO₂Me 3-136 Cl O(CH₂)₃OMe SO₂Et 3-137 Cl O(CH₂)₂OMe SO₂Me 3-138 Cl O(CH₂)₂OMe SO₂Et 3-139 Cl [1,4]dioxan-2-yl-methoxy SO₂Me 3-140 Cl [1,4]dioxan-2-yl-methoxy SO₂Et 3-141 Cl SO₂Me Me 3-142 Cl SEt Me 3-143 Cl SOEt Me 3-144 Cl SO₂Et Me 3-145 Cl 4,5-dihydro-1,3-oxazol-3-yl SO₂Me 3-146 Cl Cl SO₂Me 3-146 Cl Cl SO₂Me 3-147 F SMe CF₃ 3-148 F S(O)Me CF₃ 3-149 OMe SMe CF₃ 3-150 OMe S(O)Me CF₃ 3-151 OMe SO₂Me CF₃ 3-152 Et NH(CH₂)₂OMe SO₂Me 3-153 Et F SO₂Me 3-154 Et SMe CF₃ 3-155 CF₃ F SO₂Me 3-156 CF₃ F SO₂Et 3-157 CF₃ O(CH₂)₂OMe SO₂Et 3-158 CF₃ O(CH₂)₃OMe SO₂Et 3-159 CF₃ O(CH₂)₂OMe SO₂Me 3-160 CF₃ O(CH₂)₃OMe SO₂Me 3-161 CF₃ OCH₂CONMe₂ SO₂Me 3-162 CF₃ OCH₂CONMe₂ SO₂Et 3-163 CF₃ OCH₂CONMe₂ Cl 3-164 CF₃ OCH₂CONMe₂ Br 3-165 CF₃ OCH₂CONMe₂ I 3-166 CF₃ OCH₂CONMe₂ F 3-167 CF₃ O(CH₂)₂OMe Cl 3-168 CF₃ O(CH₂)₃OMe Cl 3-169 CF₃ O(CH₂)₂OMe Br 3-170 CF₃ O(CH₂)₃OMe Br 3-171 CF₃ O(CH₂)₂OMe I 3-172 CF₃ O(CH₂)₃OMe I 3-173 CF₃ O(CH₂)₂OMe F 3-174 CF₃ O(CH₂)₃OMe F 3-175 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Me 3-176 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Et 3-177 CF₃ [1,4]dioxan-2-yl-methoxy Cl 3-178 CF₃ [1,4]dioxan-2-yl-methoxy Br 3-179 CF₃ [1,4]dioxan-2-yl-methoxy I 3-180 CF₃ [1,4]dioxan-2-yl-methoxy F 3-181 Br OMe Br 3-182 Br O(CH₂)₂OMe Br 3-183 Br O(CH₂)₄OMe SO₂Me 3-184 Br O(CH₂)₄OMe SO₂Et 3-185 Br O(CH₂)₃OMe SO₂Me 3-186 Br O(CH₂)₃OMe SO₂Et 3-187 Br O(CH₂)₂OMe SO₂Me 3-188 Br O(CH₂)₂OMe SO₂Et 3-189 Br [1,4]dioxan-2-yl-methoxy SO₂Me 3-190 Br [1,4]dioxan-2-yl-methoxy SO₂Et 3-191 Br SMe Me 3-192 Br SOMe Me 3-193 Br SO₂Me Me 3-194 Br SEt Me 3-195 Br SOEt Me 3-196 Br SO₂Et Me 3-197 I O(CH₂)₄OMe SO₂Me 3-198 I O(CH₂)₄OMe SO₂Et 3-199 I O(CH₂)₃OMe SO₂Me 3-200 I O(CH₂)₃OMe SO₂Et 3-201 I O(CH₂)₂OMe SO₂Me 3-202 I O(CH₂)₂OMe SO₂Et 3-203 I [1,4]dioxan-2-yl-methoxy SO₂Me 3-204 I [1,4]dioxan-2-yl-methoxy SO₂Et 3-205 I SMe Me 3-206 I SOMe Me 3-207 I SO₂Me Me 3-208 I SEt Me 3-209 I SOEt Me 3-210 I SO₂Et Me 3-211 CH₂SMe OMe SO₂Me 3-212 CH₂OMe OMe SO₂Me 3-213 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 3-214 CH₂O(CH₂)₂ NH(CH₂)₃OEt SO₂Me OMe 3-215 CH₂O(CH₂)₃ OMe SO₂Me OMe 3-216 CH₂O(CH₂)₂ NH(CH₂)₂OMe SO₂Me OMe 3-217 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 3-218 SO₂Me NH₂ CF₃ 3-219 SO₂Me F CF₃ 3-220 SO₂Me NHEt Cl 3-221 SMe SEt F 3-222 SMe SMe F 3-223 Me NH₂ Cl 3-224 Me NH₂ Br 3-225 Me NHMe Cl 3-226 Me NHMe Br 3-227 Me NMe₂ Cl 3-228 Me NMe₂ Br 3-227 Me NMe₂ Cl 3-228 Me NMe₂ Br 3-229 NO₂ O(CH₂)₂OMe Me 3-230 CF₃ S(O)₂Et SO₂Me 3-231 CF₃ S(O)₂Et SO₂Et 3-232 CF₃ SCH₂CONMe₂ SO₂Me 3-233 CF₃ SCH₂CONMe₂ SO₂Et 3-234 CF₃ SCH₂COOH SO₂Me 3-235 CF₃ SCH₂COOH SO₂Et 3-236 Me SO₂—CH₂—CH₂—CH═CH₂ CF₃ 3-237 Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.45 (s, 1 H), 8.02 (d, 1 H), 7.76 (d, 1 H), 3.43 (q, 2 H), 3.25 (m, 1 H), 2.75 (s, 3 H), 1.31 (d, 6 H), 1.15 (t, 3 H) 3-238 CF₃ SEt SO₂Me 3-239 OMe NO₂ Cl 3-240 OMe NH(CO)i-Pr Cl 3-241 OMe NH(CO)CH₂Ph Cl 3-242 CF₃ SEt SO₂Et 3-243 CF₃ S(O)Et SO₂Me 3-244 Cl Me Cl 3-245 Me 3,5-dimethylpyrazol-1-yl SO₂Me 3-247 Me 1,2,3-triazol-1-yl SO₂Me 3-248 Me Me SMe 3-249 Me pyrrolidin-2-on-1-yl SO₂Me 3-250 CF₃ S(O)Et SO₂Et 3-251 Cl pyrazol-1-yl SO₂Me 3-252 Me 3-methylpyrazol-1-yl SO₂Me 3-253 Cl CH₂—N(Et)OMe SO₂Me 3-254 Me Me Cl 3-255 OH Cl Cl 3-256 Me 1,2,4-triazol-1-yl SO₂Me 3-257 Me 4-methoxypyrazol-1-yl SO₂Me 3-258 Me 1,2,4-triazol-1-yl CF₃ 3-259 Me tetrahydro-pyrimidin-2(1H)- SO₂Me on-1-yl 3-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me 3-261 Me NH—iPr SO₂Me 3-262 Cl NH—CH₂—(CO)NHEt Cl 3-263 Me NH—CH₂—(CO)NMe₂ SO₂Me 3-264 Me NH—CH₂-furan-2-yl SO₂Me 3-265 Me NH—CH₂—(CO)NHEt SO₂Me 3-266 Me F SO₂Me 3-267 F SO₂Me SO₂Me 3-268 Cl (4-cyclopropyl-3-methyl-5- Cl oxo-4,5-dihydro-1H-1,2,4- triazol-1-yl)methyl 3-269 Cl [4-methyl-5-oxo-3-(2,2,2- Cl trifluoro-ethoxy)-4,5-dihydro- 1H-1,2,4-triazol-1-yl]methyl 3-270 Cl (3-isopropoxy-4-methyl-5- Cl oxo-4,5-dihydro-1H-1,2,4- triazol-1-yl]methyl 3-271 Cl (4-methyl-5-oxo-4,5-dihydro- Cl 1H-1,2,4-triazol-1-yl)methyl 3-272 Me Cl SO₂Et 3-273 SO₂Me F Cl 3-274 Me 1,2,3-triazol-1-yl SO₂Me 3-275 Me isobutyl(methyl)- SO₂Me carbamoylamino 3-276 Me 3-oxomorpholin-4-yl SO₂Me 3-277 OMe [ethyl(methyl-sulfonyl)-amino] Cl methyl 3-278 F SO₂Me CF₃ 3-279 OMe benzoylamino Cl 3-280 OMe cyclopropylcarbonyl- Cl amino 3-281 OMe propionylamino Cl 3-282 NO₂ SO₂Me SO₂Me 3-283 NO₂ SO₂Me Cl 3-284 NO₂ SOMe SO₂Me 3-285 NO₂ SOMe Br 3-286 NO₂ SOMe Cl 3-287 NO₂ SMe SO₂Me 3-288 NO₂ SMe Br 3-289 NO₂ SMe Cl 3-290 Cl CH₂OCH(CH₃)₂ SO₂Et 3-291 Cl CH₂OEt SO₂Et 3-292 Cl CH₂OMe SO₂Et 3-293 Cl CH₂OCH₂C₂F₅ SO₂Me 3-294 Cl CH₂OCH₂CHF₂ SO₂Me 3-295 Cl CH₂OCH₂CCH SO₂Et 3-296 Cl CH₂OC₂H₄OMe SO₂Me 3-297 Cl CH₂(OC₂H₄)₂OMe SO₂Me 3-298 Cl 5-ethoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 3-299 Cl 5-methoxymethyl- SO₂Et 4,5-dihydro-1,2-oxazol- oxazol-3-yl 3-300 Et SOMe CF₃ 3-301 iPr SMe CF₃ 3-302 Et SMe CF₃ 3-303 Et SO₂Me CF₃ 3-304 cPr SOMe CF₃ 3-305 CH═CH₂ SMe CF₃ 3-306 Et SMe Cl 3-307 Et SO₂Me Cl 3-308 Cl NMe₂ Cl 3-309 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 3-313 Me SO₂(CH₂)₂OMe CF₃ 3-314 Me SOEt SO₂Me 3-315 Me SO₂Et SO₂Me 3-316 Me SMe 1,2,4- triazol-1- yl 3-317 OEt SMe CF₃ 3-318 Me S(CH₂)₂OMe CF₃ 3-319 Me SOMe 1,2,4- triazol-1- yl 3-320 OEt SOMe CF₃ 3-321 Me SO(CH₂)₂OMe CF₃ 3-322 Me SCH₂CCMe SO₂Me 3-323 Me S-c-Pen SO₂Me 3-324 OMe SMe OMe 3-325 Me SCH₂CH═CHCH₃ SO₂Me 3-326 Me SOCH₂CCMe SO₂Me 3-327 Me SO₃-c-Pen SO₂Me 3-328 Me SO-c-Pen SO₂Me 3-329 Me S(CH₂)₃Cl SO₂Me 3-330 Me SCH₂(4-F—Ph) SO₂Me 3-331 Me SO₂CH₂CCMe SO₂Me 3-332 Me SO₂CH₂CH═CHCH₃ SO₂Me 3-333 Me SOCH₂CH═CHCH₃ SO₂Me 3-334 Me SOCH₂-epoxy-Me SO₂Me 3-335 Me SO₂(CH₂)₃Cl SO₂Me 3-336 Me SO(CH₂)₃Cl SO₂Me 3-337 Me SOCH₂(4-F—Ph) SO₂Me 3-338 Me SO₂CH₂(4-F—Ph) SO₂Me 3-339 Me SO₂Me C₂F₅ 3-340 O(CH₂)₂OMe SMe CF₃ 3-341 O(CH₂)₂OMe SO₂Me CF₃ 3-342 O(CH₂)₂OMe SOMe CF₃ 3-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me 3-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me 3-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me 3-346 OEt SEt CF₃ 3-347 O—CH₂-c-Pr SMe CF₃ 3-348 OMe SEt CF₃ 3-349 OMe SO₂Et CF₃ 3-350 OMe SOEt CF₃ 3-351 OEt SO₂Et CF₃ 3-352 OEt SOEt CF₃ 3-353 O—CH₂-c-Pr SOMe CF₃ 3-354 O—CH₂-c-Pr SO₂Me CF₃ 3-355 Me SEt SO₂Me

TABLE 4 Compounds of the general formula (I) according to the invention in which R is propyl

No. X Y Z Physical data 4-1  CF₃ OCH₂CON(Me)Et SO₂Me 4-2  CF₃ OCH₂CON(Me)Et SO₂Et 4-4  CF₃ 2-(1H-pyrazol-1-yl)- SO₂Me ethoxyl 4-5  CF₃ 2-(1H-pyrazol-1-yl)- SO₂Et ethoxyl 4-6  CF₃ tetrahydrofuran-2-yl- SO₂Me methoxy 4-7  CF₃ tetrahydrofuran-2-yl- SO₂Et methoxy 4-8  CF₃ OH SO₂Me 4-9  CF₃ OH SO₂Et 4-10  CF₃ SH SO₂Me 4-11  CF₃ SH SO₂Et 4-15  CF₃ SMe SO₂Me 4-16  CF₃ SMe SO₂Et 4-17  CF₃ S(O)Me SO₂Me 4-24  CF₃ S(O)Me SO₂Et 4-25  CF₃ S(O)₂Me SO₂Me 4-26  CF₃ S(O)₂Me SO₂Et 4-27  CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethoxy 4-28  CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethyl}sulfanyl 4-29  CF₃ 2-[(methylsulfonyl)- SO₂Et amino]ethyl}sulfanyl 4-30  NO₂ O(CH₂)₂OMe OMe 4-31  NO₂ OMe Me 4-32  NO₂ NH₂ OMe 4-33  NO₂ NH₂ SO₂Et 4-34  NO₂ NH₂ Cl 4-35  NO₂ NHMe Cl 4-36  NO₂ NMe₂ Cl 4-37  NO₂ NH₂ Br 4-38  NO₂ NHMe Br 4-39  NO₂ NMe₂ Br 4-40  NO₂ NH₂ F 4-41  NO₂ NHMe F 4-42  NO₂ NMe₂ F 4-43  NO₂ NH₂ SO₂Me 4-44  NO₂ NHMe SO₂Me 4-45  NO₂ NMe₂ SO₂Me 4-46  NO₂ NH₂ 1H-1,2,4- triazol-1- yl 4-47  NO₂ NHMe 1H-1,2,4- triazol-1- yl 4-48  NO₂ NMe₂ 1H-1,2,4- triazol-1- yl 4-49  Me F F 4-50  Me F Cl 4-51  Me SMe CF₃ 4-52  Me Cl SO₂Me 4-53  Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.48 (s, 1 H), 8.28 (d, 1 H), 8.08 (d, 1 H), 3.61 (s, 3 H), 3.58 (s, 3 H), 2.79 (t, 2 H), 2.70 (s, 3 H), 1.71 (m, 2 H), 0.94 (t, 3 H) 4-54  Me SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.59 (bs, 1 H), 7.87 (d, 1 H), 7.76 (d, 1 H), 3.20 (s, 3 H), 2.83 (t, 2 H), 2.78 (s, 3 H), 1.83 (m, 2 H), 1.05 (t, 3 H) 4-55  Me Cl CF₃ 4-56  Me S(O)Me CF₃ 4-57  Me SEt OMe 4-58  Me NMe₂ SO₂Me 4-59  Me NH(CH₂)₂OMe SO₂Me 4-60  Me O(CH₂)₄OMe SO₂Me 4-61  Me NH₂ SO₂Me 4-62  Me O(CH₂)₂—O(3,5-di- SO₂Me methoxypyrimidin-2-yl 4-63  Me O(CH₂)₂—O—NMe₂ Cl 4-64  Me O(CH₂)₂—NH(CO)NMe₂ Cl 4-65  Me O(CH₂)-5-pyrrolidin- Br 2-one 4-66  Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 4-67  Me O(CH₂)—(CO)NEt₂ Br 4-68  Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H-1,2,4- triazol-3-one 4-69  Me O(CH₂)-3,5- Cl dimethyl-1,2-oxazol- 4-yl 4-70  Me O(CH₂)₂—NHCO₂Me Cl 4-71  Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 4-72  Me Me SO₂Me 4-73  Me OH SO₂Me 4-74  Me O—CH₂—NHSO₂cPr Cl 4-75  Me O(CH₂)₂NHSO2Me SO₂Me 4-76  Me S(O)Me SO₂Me 4-77  Me SMe SO₂Me 4-78  Me SMe OMe 4-79  Me S(O)Me OMe 4-80  Me SO₂Me OMe 4-81  Me SMe Cl 4-82  Me S(O)Me Cl 4-83  Me SO₂Me Cl 4-84  Me [1,4]dioxan-2-yl- SO₂Me methoxy 4-85  Me [1,4]dioxan-2-yl- SO₂Et methoxy 4-86  Me O(CH₂)₄OMe SO₂Et 4-87  Me O(CH₂)₃OMe SO₂Me 4-88  Me O(CH₂)₃OMe SO₂Et 4-89  Me O(CH₂)₂OMe SO₂Me 4-90  Me O(CH₂)₂OMe SO₂Et 4-91  Me S(O)Me SO₂Me 4-92  Me SMe SO₂Me 4-93  Me SMe OMe 4-94  Me S(O)Me OMe 4-95  Me SO₂Me OMe 4-96  Me SMe Cl 4-97  Me S(O)Me Cl 4-98  Me SO₂Me Cl 4-99  Me SMe Br 4-100 Me SOMe Br 4-101 Me SO₂Me Br 4-102 Me SMe I 4-103 Me SOMe I 4-104 Me SO₂Me I 4-105 Me SEt Cl 4-106 Me SOEt Cl 4-107 Me SO₂Et Cl 4-108 Me SEt Br 4-109 Me SOEt Br 4-110 Me SO₂Et Br 4-111 Me SEt I 4-112 Me SOEt I 4-113 Me SO₂Et I 4-114 Me SEt F 4-115 Me SOEt F 4-116 Me SO₂Et F 4-117 Cl OCH₂(CO)NMe₂ Cl 4-118 Cl Cl SO₂Me 4-119 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.40 (bs, 1 H), 8.05 (d, 1 H), 7.76 (d, 1 H), 5.33 (s, 2 H), 4.05 (q, 2 H), 3.22 (s, 3 H), 2.86 (t, 2 H), 1.84 (m, 2 H), 1.05 (t, 3 H) 4-120 Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, CDCl₃, 400 MHz dihydro-1,2-oxazol-3-yl 8.19 (bs, 1 H), 8.13 (d, 1 H), 7.95 (d, 1 H), 5.17 (m, 1 H), 3.73 (m, 1 H), 3.36 (q, 2 H), 3.25 (m, 1 H), 2.86 (m, 4 H), 1.82 (m, 2 H), 1.30 (t, 3 H), 1.05 (t, 3 H) 4-121 Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 4-122 Cl CH₂O- SO₂Me tetrahydrofuran-2-yl 4-123 Cl SMe SO₂Me 4-124 Cl F SMe 4-125 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 4-126 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 4-127 Cl O(CH₂)-5-pyrrolidin-2- Cl one 4-128 Cl SMe Cl 4-129 Cl S(O)Me SO₂Me 4-130 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 4-131 Cl O(CH₂)₂OMe Cl 4-132 Cl O(CH₂)₂OMe SO₂Me 4-133 Cl O(CH₂)₄OMe SO₂Me 4-134 Cl O(CH₂)₄OMe SO₂Et 4-135 Cl O(CH₂)₃OMe SO₂Me 4-136 Cl O(CH₂)₃OMe SO₂Et 4-137 Cl O(CH₂)₂OMe SO₂Me 4-138 Cl O(CH₂)₂OMe SO₂Et 4-139 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 4-140 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 4-141 Cl SO₂Me Me 4-142 Cl SEt Me 4-143 Cl SOEt Me 4-144 Cl SO₂Et Me 4-145 Cl 4,5-dihydro-1,4- SO₂Me oxazol-3-yl 4-146 Cl Cl SO₂Me 4-147 F SMe CF₃ 4-148 F S(O)Me CF₃ 4-149 OMe SMe CF₃ 4-150 OMe S(O)Me CF₃ 4-151 OMe SO₂Me CF₃ 4-152 Et NH(CH₂)₂OMe SO₂Me 4-153 Et F SO₂Me 4-154 Et SMe CF₃ 4-155 CF₃ F SO₂Me 4-156 CF₃ F SO₂Et 4-157 CF₃ O(CH₂)₂OMe SO₂Et 4-158 CF₃ O(CH₂)₃OMe SO₂Et 4-159 CF₃ O(CH₂)₂OMe SO₂Me 4-160 CF₃ O(CH₂)₃OMe SO₂Me 4-161 CF₃ OCH₂CONMe₂ SO₂Me 4-162 CF₃ OCH₂CONMe₂ SO₂Et 4-163 CF₃ OCH₂CONMe₂ Cl 4-164 CF₃ OCH₂CONMe₂ Br 4-165 CF₃ OCH₂CONMe₂ I 4-166 CF₃ OCH₂CONMe₂ F 4-167 CF₃ O(CH₂)₂OMe Cl 4-168 CF₃ O(CH₂)₃OMe Cl 4-169 CF₃ O(CH₂)₂OMe Br 4-170 CF₃ O(CH₂)₃OMe Br 4-171 CF₃ O(CH₂)₂OMe I 4-172 CF₃ O(CH₂)₃OMe I 4-173 CF₃ O(CH₂)₂OMe F 4-174 CF₃ O(CH₂)₃OMe F 4-175 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 4-176 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 4-177 CF₃ [1,4]dioxan-2-yl- Cl methoxy 2-178 CF₃ [1,4]dioxan-2-yl- Br methoxy 4-179 CF₃ [1,4]dioxan-2-yl- I methoxy 4-180 CF₃ [1,4]dioxan-2-yl- F methoxy 4-181 Br OMe Br 4-182 Br O(CH₂)₂OMe Br 4-183 Br O(CH₂)₄OMe SO₂Me 4-184 Br O(CH₂)₄OMe SO₂Et 4-185 Br O(CH₂)₃OMe SO₂Me 4-186 Br O(CH₂)₃OMe SO₂Et 4-187 Br O(CH₂)₂OMe SO₂Me 4-188 Br O(CH₂)₂OMe SO₂Et 4-189 Br [1,4]dioxan-2-yl- SO₂Me methoxy 4-190 Br [1,4]dioxan-2-yl- SO₂Et methoxy 4-191 Br SMe Me 4-192 Br SOMe Me 4-193 Br SO₂Me Me 4-194 Br SEt Me 4-195 Br SOEt Me 4-196 Br SO₂Et Me 4-197 I O(CH₂)₄OMe SO₂Me 4-198 I O(CH₂)₄OMe SO₂Et 4-199 I O(CH₂)₃OMe SO₂Me 4-200 I O(CH₂)₃OMe SO₂Et 4-201 I O(CH₂)₂OMe SO₂Me 4-202 I O(CH₂)₂OMe SO₂Et 4-203 I [1,4]dioxan-2-yl- SO₂Me methoxy 4-204 I [1,4]dioxan-2-yl- SO₂Et methoxy 4-205 I SMe Me 4-206 I SOMe Me 4-207 I SO₂Me Me 4-208 I SEt Me 4-209 I SOEt Me 4-210 I SO₂Et Me 4-211 CH₂SMe OMe SO₂Me 4-212 CH₂OMe OMe SO₂Me 4-213 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 4-214 CH₂O(CH₂)₂ NH(CH₂)₃OEt SO₂Me OMe 4-215 CH₂O(CH₂)₃ OMe SO₂Me OMe 4-216 CH₂O(CH₂)₂ NH(CH₂)₂OMe SO₂Me OMe 4-217 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 4-218 SO₂Me NH₂ CF₃ 4-219 SO₂Me F CF₃ 4-220 SO₂Me NHEt Cl 4-221 SMe SEt F 4-222 SMe SMe F 4-223 Me NH₂ Cl 4-224 Me NH₂ Br 4-225 Me NHMe Cl 4-226 Me NHMe Br 4-227 Me NMe₂ Cl 4-228 Me NMe₂ Br 4-227 Me NMe₂ Cl 4-228 Me NMe₂ Be 4-229 NO₂ O(CH₂)₂OMe Me 4-230 CF₃ S(O)₂Et SO₂Me 4-231 CF₃ S(O)₂Et SO₂Et 4-232 CF₃ SCH₂CONMe₂ SO₂Me 4-233 CF₃ SCH₂CONMe₂ SO₂Et 4-234 CF₃ SCH₂COOH SO₂Me 4-235 CF₃ SCH₂COOH SO₂Et 4-236 Me SO₂—CH₂—CH₂—CH═CH₂ CF₃ 4-237 Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.45 (s, 1 H), 8.02 (d, 1 H), 7.76 (d, 1 H), 3.43 (q, 2 H), 3.25 (m, 1 H), 2.75 (s, 3 H), 1.31 (d, 6 H), 1.15 (t, 3 H) 4-238 CF₃ SEt SO₂Me 4-239 OMe NO₂ Cl 4-240 OMe NH(CO)i-Pr Cl 4-241 OMe NH(CO)CH₂Ph Cl 4-242 CF₃ SEt SO₂Et 4-243 CF₃ S(O)Et SO₂Me 4-244 Cl Me Cl 4-245 Me 3,5-dimethylpyrazol- SO₂Me 1-yl 4-247 Me 1,2,3-triazol-1-yl SO₂Me 4-248 Me Me SMe 4-249 Me pyrrolidin-2-on-1-yl SO₂Me 4-250 CF₃ S(O)Et SO₂Et 4-251 Cl pyrazol-1-yl SO₂Me 4-252 Me 3-methylpyrazol-1-yl SO₂Me 4-253 Cl CH₂—N(Et)OMe SO₂Me 4-254 Me Me Cl 4-255 OH Cl Cl 4-256 Me 1,2,4-triazol-1-yl SO₂Me 4-257 Me 4-methoxypyrazol-1-yl SO₂Me 4-258 Me 1,2,4-triazol-1-yl CF₃ 4-259 Me tetrahydro- SO₂Me pyrimidin-2(1H)-on- 1-yl 4-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me 4-261 Me NH—iPr SO₂Me 4-262 Cl NH—CH₂—(CO)NHEt Cl 4-263 Me NH—CH₂—(CO)NMe₂ SO₂Me 4-264 Me NH—CH₂-furan-2-yl SO₂Me 4-265 Me NH—CH₂—(CO)NHEt SO₂Me 4-266 Me F SO₂Me 4-267 F SO₂Me SO₂Me 4-268 Cl (4-cyclopropyl-3- Cl methyl-5-oxo-4,5- dihydro-1H-1,2,4- triazol-1-yl)methyl 4-269 Cl [4-methyl-5-oxo-3- Cl (2,2,2-trifluoro- ethoxy)-4,5-dihydro- 1H-1,2,4-triazol-1- yl]methyl 4-270 Cl (3-isopropoxy-4- Cl methyl-5-oxo-4,5- dihydro-1H-1,2,4- triazol-1-yl]methyl 4-271 Cl (4-methyl-5-oxo-4,5- Cl dihydro-1H-1,2,4- triazol-1-yl)methyl 4-272 Me Cl SO₂Et 4-273 SO₂Me F Cl 4-274 Me 1,2,3-triazol-1-yl SO₂Me 4-275 Me isobutyl(methyl)- SO₂Me carbamoylamino 4-276 Me 3-oxomorpholin-4-yl SO₂Me 4-277 OMe [ethyl(methyl- Cl sulfonyl)-amino] methyl 4-278 F SO₂Me CF₃ 4-279 OMe benzoylamino Cl 4-280 OMe cyclopropylcarbonyl- Cl amino 4-281 OMe propionylamino Cl 4-282 NO₂ SO₂Me SO₂Me 4-283 NO₂ SO₂Me Cl 4-284 NO₂ SOMe SO₂Me 4-285 NO₂ SOMe Br 4-286 NO₂ SOMe Cl 4-287 NO₂ SMe SO₂Me 4-288 NO₂ SMe Br 4-289 NO₂ SMe Cl 4-290 Cl CH₂OCH(CH₃)₂ SO₂Et 4-291 Cl CH₂OEt SO₂Et 4-292 Cl CH₂OMe SO₂Et 4-293 Cl CH₂OCH₂C₂F₅ SO₂Me 4-294 Cl CH₂OCH₂CHF₂ SO₂Me 4-295 Cl CH₂OCH₂CCH SO₂Et 4-296 Cl CH₂OC₂H₄OMe SO₂Me 4-297 Cl CH₂(OC₂H₄)₂OMe SO₂Me 4-298 Cl 5-ethoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 4-299 Cl 5-methoxymethyl- SO₂Et 4,5-dihydro-1,2-oxazol- oxazol-3-yl 4-300 Et SOMe CF₃ 4-301 iPr SMe CF₃ 4-302 Et SMe CF₃ 4-303 Et SO₂Me CF₃ 4-304 cPr SOMe CF₃ 4-305 CH═CH₂ SMe CF₃ 4-306 Et SMe Cl 4-307 Et SO₂Me Cl 4-308 Cl NMe₂ Cl 4-309 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 4-313 Me SO₂(CH₂)₂OMe CF₃ 4-314 Me SOEt SO₂Me 4-315 Me SO₂Et SO₂Me 4-316 Me SMe 1,2,4- triazol-1- yl 4-317 OEt SMe CF₃ 4-318 Me S(CH₂)₂OMe CF₃ 4-319 Me SOMe 1,2,4- triazol-1- yl 4-320 OEt SOMe CF₃ 4-321 Me SO(CH₂)₂OMe CF₃ 4-322 Me SCH₂CCMe SO₂Me 4-323 Me S-c-Pen SO₂Me 4-324 OMe SMe OMe 4-325 Me SCH₂CH═CHCH₃ SO₂Me 4-326 Me SOCH₂CCMe SO₂Me 4-327 Me SO₄-c-Pen SO₂Me 4-328 Me SO-c-Pen SO₂Me 4-329 Me S(CH₂)₃Cl SO₂Me 4-330 Me SCH₂(4-F—Ph) SO₂Me 4-331 Me SO₂CH₂CCMe SO₂Me 4-332 Me SO₂CH₂CH═CHCH₃ SO₂Me 4-333 Me SOCH₂CH═CHCH₃ SO₂Me 4-334 Me SOCH₂-epoxy-Me SO₂Me 4-335 Me SO₂(CH₂)₃Cl SO₂Me 4-336 Me SO(CH₂)₃Cl SO₂Me 4-337 Me SOCH₂(4-F—Ph) SO₂Me 4-338 Me SO₂CH₂(4-F—Ph) SO₂Me 4-339 Me SO₂Me C₂F₅ 4-340 O(CH₂)₂OMe SMe CF₃ 4-341 O(CH₂)₂OMe SO₂Me CF₃ 4-342 O(CH₂)₂OMe SOMe CF₃ 4-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me 4-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me 4-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me 4-346 OEt SEt CF₃ 4-347 O—CH₂-c-Pr SMe CF₃ 4-348 OMe SEt CF₃ 4-349 OMe SO₂Et CF₃ 4-350 OMe SOEt CF₃ 4-351 OEt SO₂Et CF₃ 4-352 OEt SOEt CF₃ 4-353 O—CH₂-c-Pr SOMe CF₃ 4-354 O—CH₂-c-Pr SO₂Me CF₃ 4-355 Me SEt SO₂Me

TABLE 5 Compounds of the general formula (I) according to the invention in which R is chloromethyl

No. X Y Z Physical data 5-1 CF₃ OCH₂CON(Me)Et SO₂Me 5-2 CF₃ OCH₂CON(Me)Et SO₂Et 5-4 CF₃ 2-(1H-pyrazol-1- SO₂Me yl)ethoxyl 5-5 CF₃ 2-(1H-pyrazol-1- SO₂Et yl)ethoxyl 5-6 CF₃ tetrahydrofuran-2-yl- SO₂Me methoxy 5-7 CF₃ tetrahydrofuran-2-yl- SO₂Et methoxy 5-8 CF₃ OH SO₂Me 5-9 CF₃ OH SO₂Et 5-10 CF₃ SH SO₂Me 5-11 CF₃ SH SO₂Et 5-15 CF₃ SMe SO₂Me 5-16 CF₃ SMe SO₂Et 5-17 CF₃ S(O)Me SO₂Me 5-24 CF₃ S(O)Me SO₂Et 5-25 CF₃ S(O)₂Me SO₂Me 5-26 CF₃ S(O)₂Me SO₂Et 5-27 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethoxy 5-28 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethyl}sulfanyl 5-29 CF₃ 2-[(methylsulfonyl)- SO₂Et amino]ethyl}sulfanyl 5-30 NO₂ O(CH₂)₂OMe OMe 5-31 NO₂ OMe Me 5-32 NO₂ NH₂ OMe 5-33 NO₂ NH₂ SO₂Et 5-34 NO₂ NH₂ Cl 5-35 NO₂ NHMe Cl 5-36 NO₂ NMe₂ Cl 5-37 NO₂ NH₂ Br 5-38 NO₂ NHMe Br 5-39 NO₂ NMe₂ Br 5-40 NO₂ NH₂ F 5-41 NO₂ NHMe F 5-42 NO₂ NMe₂ F 5-43 NO₂ NH₂ SO₂Me 5-44 NO₂ NHMe SO₂Me 5-45 NO₂ NMe₂ SO₂Me 5-46 NO₂ NH₂ 1H-1,2,4- triazol-1-yl 5-47 NO₂ NHMe 1H-1,2,4- triazol-1-yl 5-48 NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 5-49 Me F F 5-50 Me F Cl 5-51 Me SMe CF₃ 5-52 Me Cl SO₂Me 5-53 Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.89 (s, 1H), 8.29 (d, 1H), 8.08 (d, 1H), 5.08 (s, 2H), 3.61 (s, 3H), 3.57 (s, 3H), 2.71 (s, 3H) 5-54 Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.89 (s, 1H), 8.08 (d, 1H), 8.01 (d, 1H), 5.09 (s, 2H), 3.43 (s, 3H), 2.73 (s, 3H) 5-55 Me Cl CF₃ 5-56 Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.86 (s, 1H), 7.91 (d, 1H), 7.87 (d, 1H), 5.09 (s, 2H), 3.05 (s, 3H), 2.87 (s, 3H) 5-57 Me SEt OMe 5-58 Me NMe₂ SO₂Me 5-59 Me NH(CH₂)₂OMe SO₂Me 5-60 Me O(CH₂)₄OMe SO₂Me 5-61 Me NH₂ SO₂Me 5-62 Me O(CH₂)₂—O(3,5-di- SO₂Me methoxypyrimidin-2-yl 5-63 Me O(CH₂)₂—O—NMe₂ Cl 5-64 Me O(CH₂)₂—NH(CO)NMe₂ Cl 5-65 Me O(CH₂)-5-pyrrolidin-2- Br one 5-66 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 5-67 Me O(CH₂)—(CO)NEt₂ Br 5-68 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one 5-69 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 5-70 Me O(CH₂)₂—NHCO₂Me Cl 5-71 Me 4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 5-72 Me Me SO₂Me 5-73 Me OH SO₂Me 5-74 Me O—CH₂—NHSO₂cPr Cl 5-75 Me O(CH₂)₂NHSO₂Me SO₂Me 5-76 Me S(O)Me SO₂Me 5-77 Me SMe SO₂Me 5-78 Me SMe OMe 5-79 Me S(O)Me OMe 5-80 Me SO₂Me OMe 5-81 Me SMe Cl 5-82 Me S(O)Me Cl 5-83 Me SO₂Me Cl 5-84 Me [1,4]dioxan-2-yl- SO₂Me methoxy 5-85 Me [1,4]dioxan-2-yl- SO₂Et methoxy 5-86 Me O(CH₂)₄OMe SO₂Et 5-87 Me O(CH₂)₃OMe SO₂Me 5-88 Me O(CH₂)₃OMe SO₂Et 5-89 Me O(CH₂)₂OMe SO₂Me 5-90 Me O(CH₂)₂OMe SO₂Et 5-91 Me S(O)Me SO₂Me 5-92 Me SMe SO₂Me 5-93 Me SMe OMe 5-94 Me S(O)Me OMe 5-95 Me SO₂Me OMe 5-96 Me SMe Cl 5-97 Me S(O)Me Cl 5-98 Me SO₂Me Cl 5-99 Me SMe Br 5-100 Me SOMe Br 5-101 Me SO₂Me Br 5-102 Me SMe I 5-103 Me SOMe I 5-104 Me SO₂Me I 5-105 Me SEt Cl 5-106 Me SOEt Cl 5-107 Me SO₂Et Cl 5-108 Me SEt Br 5-109 Me SOEt Br 5-110 Me SO₂Et Br 5-111 Me SEt I 5-112 Me SOEt I 5-113 Me SO₂Et I 5-114 Me SEt F 5-115 Me SOEt F 5-116 Me SO₂Et F 5-117 Cl OCH₂(CO)NMe₂ Cl 5-118 Cl Cl SO₂Me 5-119 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.60 (bs, 1H), 8.10 (d, 1H), 7.83 (d, 1H), 5.35 (s, 2H), 5.0 (s, 2H), 4.06 (q, 2H), 3.23 (s, 3H) 5-120 Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz dihydro-1,2-oxazol-3-yl 12.03 (s, 1H), 8.16 (d, 1H), 8.10 (d, 1H), 5.20 (m, 1H), 5.08 (s, 2H), 3.60 (dd, 1H), 3.44 (q, 2H), 3.17 (dd, 1H), 3.05 (m, 2H), 1.16 (t, 3H) 5-121 Cl CH₂O-tetrahydrofuran- SO₂Me 3-yl 5-122 Cl CH₂O-tetrahydrofuran- SO₂Me 2-yl 5-123 Cl SMe SO₂Me 5-124 Cl F SMe 5-125 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 5-126 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 5-127 Cl O(CH₂)-5-pyrrolidin-2- Cl one 5-128 Cl SMe Cl ¹H NMR, CDCl₃, 400 MHz 12.19 (bs, 1H), 7.70 (d, 1H), 7.62 (d, 1H), 6.30 (s, 2H), 2.21 (s, 3H), 5-129 Cl S(O)Me SO₂Me 5-130 Cl CH₂O-tetrahydrofuran- SO₂Et ¹H NMR, CDCl₃, 400 MHz 3-yl 9.05 (bs, 1H), 7.97 (d, 1H), 7.75 (d, 1H), 5.07 (s, 2H), 5.02 (s, 2H), 4.34 (m, 1H), 3.72-3.92 (m, 4H), 3.37 (q, 2H), 2.08 (m, 2H), 1.25 (t, 3H) 5-131 Cl O(CH₂)₂OMe Cl 5-132 Cl O(CH₂)₂OMe SO₂Me 5-133 Cl O(CH₂)₄OMe SO₂Me 5-134 Cl O(CH₂)₄OMe SO₂Et 5-135 Cl O(CH₂)₃OMe SO₂Me 5-136 Cl O(CH₂)₃OMe SO₂Et 5-137 Cl O(CH₂)₂OMe SO₂Me 5-138 Cl O(CH₂)₂OMe SO₂Et 5-139 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 5-140 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 5-141 Cl SO₂Me Me 5-142 Cl SEt Me 5-143 Cl SOEt Me 5-144 Cl SO₂Et Me 2-145 Cl 4,5-dihydro-1,5-oxazol- SO₂Me 3-yl 5-146 Cl Cl SO₂Me 5-147 F SMe CF₃ 5-148 F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 12.05 (bs, 1H), 8.13 (dd, 1H), 7.92 (d, 1H), 5.09 (s, 2H), 3.18 (s, 3H), 5-149 OMe SMe CF₃ 5-150 OMe S(O)Me CF₃ 5-151 OMe SO₂Me CF₃ 5-152 Et NH(CH₂)₂OMe SO₂Me 5-153 Et F SO₂Me 5-154 Et SMe CF₃ 5-155 CF₃ F SO₂Me 5-156 CF₃ F SO₂Et 5-157 CF₃ O(CH₂)₂OMe SO₂Et 5-158 CF₃ O(CH₂)₃OMe SO₂Et 5-159 CF₃ O(CH₂)₂OMe SO₂Me 5-160 CF₃ O(CH₂)₃OMe SO₂Me 5-161 CF₃ OCH₂CONMe₂ SO₂Me 5-162 CF₃ OCH₂CONMe₂ SO₂Et 5-163 CF₃ OCH₂CONMe₂ Cl 5-164 CF₃ OCH₂CONMe₂ Br 5-165 CF₃ OCH₂CONMe₂ I 5-166 CF₃ OCH₂CONMe₂ F 5-167 CF₃ O(CH₂)₂OMe Cl 5-168 CF₃ O(CH₂)₃OMe Cl 5-169 CF₃ O(CH₂)₂OMe Br 5-170 CF₃ O(CH₂)₃OMe Br 5-171 CF₃ O(CH₂)₂OMe I 5-172 CF₃ O(CH₂)₃OMe I 5-173 CF₃ O(CH₂)₂OMe F 5-174 CF₃ O(CH₂)₃OMe F 5-175 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 5-176 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 5-177 CF₃ [1,4]dioxan-2-yl- Cl methoxy 2-178 CF₃ [1,4]dioxan-2-yl- Br methoxy 5-179 CF₃ [1,4]dioxan-2-yl- I methoxy 5-180 CF₃ [1,4]dioxan-2-yl- F methoxy 5-181 Br OMe Br 5-182 Br O(CH₂)₂OMe Br 5-183 Br O(CH₂)₄OMe SO₂Me 5-184 Br O(CH₂)₄OMe SO₂Et 5-185 Br O(CH₂)₃OMe SO₂Me 5-186 Br O(CH₂)₃OMe SO₂Et 5-187 Br O(CH₂)₂OMe SO₂Me 5-188 Br O(CH₂)₂OMe SO₂Et 5-189 Br [1,4]dioxan-2-yl- SO₂Me methoxy 5-190 Br [1,4]dioxan-2-yl- SO₂Et methoxy 5-191 Br SMe Me 5-192 Br SOMe Me 5-193 Br SO₂Me Me 5-194 Br SEt Me 5-195 Br SOEt Me 5-196 Br SO₂Et Me 5-197 I O(CH₂)₄OMe SO₂Me 5-198 I O(CH₂)₄OMe SO₂Et 5-199 I O(CH₂)₃OMe SO₂Me 5-200 I O(CH₂)₃OMe SO₂Et 5-201 I O(CH₂)₂OMe SO₂Me 5-202 I O(CH₂)₂OMe SO₂Et 5-203 I [1,4]dioxan-2-yl- SO₂Me methoxy 5-204 I [1,4]dioxan-2-yl- SO₂Et methoxy 5-205 I SMe Me 5-206 I SOMe Me 5-207 I SO₂Me Me 5-208 I SEt Me 5-209 I SOEt Me 5-210 I SO₂Et Me 5-211 CH₂SMe OMe SO₂Me 5-212 CH₂OMe OMe SO₂Me 5-213 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 5-214 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 5-215 CH₂O(CH₂)₂OMe OMe SO₂Me 5-216 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 5-217 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 5-218 SO₂Me NH₂ CF₃ 5-219 SO₂Me F CF₃ 5-220 SO₂Me NHEt Cl 5-221 SMe SEt F 5-222 SMe SMe F 5-223 Me NH₂ Cl 5-224 Me NH₂ Br 5-225 Me NHMe Cl 5-226 Me NHMe Br 5-227 Me NMe₂ Cl 5-228 Me NMe₂ Br 5-227 Me NMe₂ Cl 5-228 Me NMe₂ Br 5-229 NO₂ O(CH₂)₂OMe Me 5-230 CF₃ S(O)₂Et SO₂Me 5-231 CF₃ S(O)₂Et SO₂Et 5-232 CF₃ SCH₂CONMe₂ SO₂Me 5-233 CF₃ SCH₂CONMe₂ SO₂Et 5-234 CF₃ SCH₂COOH SO₂Me 5-235 CF₃ SCH₂COOH SO₂Et 5-236 Me SO₂—CH₂—CH₂—CH═CH₂ CF₃ 5-237 Cl Me SO₂Et 5-238 CF₃ SEt SO₂Me 5-239 OMe NO₂ Cl 5-240 OMe NH(CO)i-Pr Cl 5-241 OMe NH(CO)CH₂Ph Cl 5-242 CF₃ SEt SO₂Et 5-243 CF₃ S(O)Et SO₂Me 5-244 Cl Me Cl 5-245 Me 3,5-dimethylpyrazol-1-yl SO₂Me 5-247 Me 1,2,3-triazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.65 (s, 1H), 8.57 (s, 1H), 8.12 (d, 1H), 8.08 (d, 1H), 8.05 (s, 1H), 4.61 (s, 2H), 3.11 (s, 3H), 5-248 Me Me SMe ¹H NMR, DMSO-d₆, 400 MHz 11.46 (s, 1H), 7.49 (d, 1H), 7.21 (d, 1H), 5.08 (s, 2H), 2.32 (s, 3H), 2.24 (s, 3H) 5-249 Me pyrrolidin-2-on-1-yl SO₂Me 5-250 CF₃ S(O)Et SO₂Et 5-251 Cl pyrazol-1-yl SO₂Me 5-252 Me 3-methylpyrazol-1-yl SO₂Me 5-253 Cl CH₂—N(Et)OMe SO₂Me 5-254 Me Me Cl 5-255 OH Cl Cl 5-256 Me 1,2,4-triazol-1-yl SO₂Me 5-257 Me 4-methoxypyrazol-1-yl SO₂Me 5-258 Me 1,2,4-triazol-1-yl CF₃ 5-259 Me tetrahydropyrimidin- SO₂Me 2(1H)-on-1-yl 5-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me 5-261 Me NH—iPr SO₂Me 5-262 Cl NH—CH₂—(CO)NHEt Cl 5-263 Me NH—CH₂—(CO)NMe₂ SO₂Me 5-264 Me NH—CH₂-furan-2-yl SO₂Me 5-265 Me NH—CH₂—(CO)NHEt SO₂Me 5-266 Me F SO₂Me 5-267 F SO₂Me SO₂Me 5-268 Cl (4-cyclopropyl-3- Cl methyl-5-oxo-4, 5- dihydro-1H-1,2,4- triazol-1-yl)methyl 5-269 Cl [4-methyl-5-oxo-3- Cl (2,2,2-trifluoroethoxy)- 4,5-dihydro-1H-1,2,4- triazol-1-yl]methyl 5-270 Cl (3-isopropoxy-4-methyl- Cl 5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1-yl]- methyl 5-271 Cl (4-methyl-5-oxo-4,5- Cl dihydro-1H-1,2,4- triazol-1-yl)methyl 5-272 Me Cl SO₂Et 5-273 SO₂Me F Cl 5-274 Me 1,2,3-triazol-1-yl SO₂Me 5-275 Me isobutyl(methyl)- SO₂Me carbamoylamino 5-276 Me 3-oxomorpholin-4-yl SO₂Me 5-277 OMe [ethyl(methylsulfonyl)- Cl amino]methyl 5-278 F SO₂Me CF₃ 5-279 OMe benzoylamino Cl 5-280 OMe cyclopropylcarbonyl- Cl amino 5-281 OMe propionylamino Cl 5-282 NO₂ SO₂Me SO₂Me 5-283 NO₂ SO₂Me Cl 5-284 NO₂ SOMe SO₂Me 5-285 NO₂ SOMe Br 5-286 NO₂ SOMe Cl 5-287 NO₂ SMe SO₂Me 5-288 NO₂ SMe Br 5-289 NO₂ SMe Cl 5-290 Cl CH₂OCH(CH₃)₂ SO₂Et 5-291 Cl CH₂OEt SO₂Et 5-292 Cl CH₂OMe SO₂Et 5-293 Cl CH₂OCH₂C₂F₅ SO₂Me 5-294 Cl CH₂OCH₂CHF₂ SO₂Me 5-295 Cl CH₂OCH₂CCH SO₂Et 5-296 Cl CH₂OC₂H₄OMe SO₂Me 5-297 Cl CH₂(OC₂H₄)₂OMe SO₂Me 5-298 Cl 5-ethoxymethyl-4, 5- SO₂Et dihydro-1,2-oxazol-3-yl 5-299 Cl 5-Methoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-300 Et SOMe CF₃ 5-301 iPr SMe CF₃ 5-302 Et SMe CF₃ 5-303 Et SO₂Me CF₃ 5-304 cPr SOMe CF₃ 5-305 CH═CH₂ SMe CF₃ 5-306 Et SMe Cl 5-307 Et SO₂Me Cl 5-308 Cl NMe₂ Cl 5-309 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 5-313 Me SO₂(CH₂)₂OMe CF₃ 5-314 Me SOEt SO₂Me 5-315 Me SO₂Et SO₂Me 5-316 Me SMe 1,2,4- triazol-1-yl 5-317 OEt SMe CF₃ 5-318 Me S(CH₂)₂OMe CF₃ 5-319 Me SOMe 1,2,4- triazol-1-yl 5-320 OEt SOMe CF₃ 5-321 Me SO(CH₂)₂OMe CF₃ 5-322 Me SCH₂CCMe SO₂Me 5-323 Me S—c-Pen SO₂Me 5-324 OMe SMe OMe 5-325 Me SCH₂CH═CHCH₃ SO₂Me 5-326 Me SOCH₂CCMe SO₂Me 5-327 Me SO₅₋c-Pen SO₂Me 5-328 Me SO—c-Pen SO₂Me 5-329 Me S(CH₂)₃Cl SO₂Me 5-330 Me SCH₂(4-F—Ph) SO₂Me 5-331 Me SO₂CH₂CCMe SO₂Me 5-332 Me SO₂CH₂CH═CHCH₃ SO₂Me 5-333 Me SOCH₂CH═CHCH₃ SO₂Me 5-334 Me SOCH₂-epoxy-Me SO₂Me 5-335 Me SO₂(CH₂)₃Cl SO₂Me 5-336 Me SO(CH₂)₃Cl SO₂Me 5-337 Me SOCH₂(4-F—Ph) SO₂Me 5-338 Me SO₂CH₂(4-F—Ph) SO₂Me 5-339 Me SO₂Me C₂F₅ 5-340 O(CH₂)₂OMe SMe CF₃ 5-341 O(CH₂)₂OMe SO₂Me CF₃ 5-342 O(CH₂)₂OMe SOMe CF₃ 5-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me 5-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me 5-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me 5-346 OEt SEt CF₃ 5-347 O—CH₂—c-Pr SMe CF₃ 5-348 OMe SEt CF₃ 5-349 OMe SO₂Et CF₃ 5-350 OMe SOEt CF₃ 5-351 OEt SO₂Et CF₃ 5-352 OEt SOEt CF₃ 5-353 O—CH₂—c-Pr SOMe CF₃ 5-354 O—CH₂—c-Pr SO₂Me CF₃ 5-355 Me SEt SO₂Me

TABLE 6 Compounds of the general formula (I) according to the invention in which R is tert-butyl

No. X Y Z Physical data 6-1 CF₃ OCH₂CON(Me)Et SO₂Me 6-2 CF₃ OCH₂CON(Me)Et SO₂Et 6-4 CF₃ 2-(1H-pyrazol-1- SO₂Me yl)ethoxyl 6-5 CF₃ 2-(1H-pyrazol-1- SO₂Et yl)ethoxyl 6-6 CF₃ tetrahydrofuran-2-yl- SO₂Me methoxy 6-7 CF₃ tetrahydrofuran-2-yl- SO₂Et methoxy 6-8 CF₃ OH SO₂Me 6-9 CF₃ OH SO₂Et 6-10 CF₃ SH SO₂Me 6-11 CF₃ SH SO₂Et 6-15 CF₃ SMe SO₂Me 6-16 CF₃ SMe SO₂Et 6-17 CF₃ S(O)Me SO₂Me 6-24 CF₃ S(O)Me SO₂Et 6-25 CF₃ S(O)₂Me SO₂Me 6-26 CF₃ S(O)₂Me SO₂Et 6-27 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethoxy 628 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethyl}sulfanyl 6-29 CF₃ 2-[(methylsulfonyl)- SO₂Et amino]ethyl}sulfanyl 6-30 Me H NO₂ 6-31 NO₂ OMe Me 6-32 NO₂ NH₂ OMe 6-33 NO₂ NH₂ SO₂Et 6-34 NO₂ NH₂ Cl 6-35 NO₂ NHMe Cl 6-36 NO₂ NMe₂ Cl 6-37 NO₂ NH₂ Br ¹H NMR, CDCl₃, 400 MHz 9.70 (s, 2H), 8.42 (d, 1H), 8.92 (d, 1H), 1.55 (s, 9H) 6-38 NO₂ NHMe Br 6-39 NO₂ NMe₂ Br 6-40 NO₂ NH₂ F 6-41 NO₂ NHMe F 6-42 NO₂ NMe₂ F 6-43 NO₂ NH₂ SO₂Me 6-44 NO₂ NHMe SO₂Me 6-45 NO₂ NMe₂ SO₂Me 6-46 NO₂ NH₂ 1H-1,2,4- triazol-5-yl 6-47 NO₂ NHMe 1H-1,2,4- triazol-5-yl 6-48 NO₂ NMe₂ 1H-1,2,4- triazol-5-yl 6-49 Me F F 6-50 Me F Cl 6-51 Me SMe CF₃ 6-52 Me Cl SO₂Me 6-53 Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.04 (s, 1H), 8.29 (d, 1H), 7.99 (d, 1H), 3.60 (s, 3H), 3.58 (s, 3H), 2.73 (s, 3H), 1.40 (s, 9H) 6-54 Me SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 7.85-7.89 (m, 2H), 7.75 (bs, 1H), 5.15 (m, 1H), 3.20 (s, 3H), 2.81 (s, 3H), 1.47 (s, 9H) 6-55 Me Cl CF₃ 6-56 Me S(O)Me CF₃ 6-57 Me SEt OMe 6-58 Me NMe₂ SO₂Me 6-59 Me NH(CH₂)₂OMe SO₂Me 6-60 Me O(CH₂)₄OMe SO₂Me 6-61 Me NH₂ SO₂Me 6-62 Me O(CH₂)₂—O-(3,5- SO₂Me dimethoxypyrimidin- 2-yl 6-63 Me O(CH₂)₂—O—NMe₂ Cl 6-64 Me O(CH₂)₂—NH(CO)NMe₂ Cl 6-65 Me O(CH₂)-5-pyrrolidin- Br 2-one 6-66 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 6-67 Me O(CH₂)—(CO)NEt₂ Br 6-68 Me O(CH₂)-5-2,4- Cl dimethyl-2,4-dihydro- 3H-1,2,4-triazol-3- one 6-69 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 6-70 Me O(CH₂)₂—NHCO₂Me Cl 6-71 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 6-72 Me Me SO₂Me 6-73 Me OH SO₂Me 6-74 Me O—CH₂—NHSO₂cPr Cl 6-75 Me O(CH₂)₂NHSO₂Me SO₂Me 6-76 Me S(O)Me SO₂Me 6-77 Me SMe SO₂Me 6-78 Me SMe OMe 6-79 Me S(O)Me OMe 6-80 Me SO₂Me OMe 6-81 Me SMe Cl 6-82 Me S(O)Me Cl 6-83 Me SO₂Me Cl 6-84 Me [1,4]dioxan-2-yl- SO₂Me methoxy 6-85 Me [1,4]dioxan-2-yl- SO₂Et methoxy 6-86 Me O(CH₂)₄OMe SO₂Et 6-87 Me O(CH₂)₃OMe SO₂Me 6-88 Me O(CH₂)₃OMe SO₂Et 6-89 Me O(CH₂)₂OMe SO₂Me 6-90 Me O(CH₂)₂OMe SO₂Et 6-91 Me S(O)Me SO₂Me 6-92 Me SMe SO₂Me 6-93 Me SMe OMe 6-94 Me S(O)Me OMe 6-95 Me SO₂Me OMe 6-96 Me SMe Cl 6-97 Me S(O)Me Cl 6-98 Me SO₂Me Cl 6-99 Me SMe Br 6-100 Me SOMe Br 6-101 Me SO₂Me Br 6-102 Me SMe I 6-103 Me SOMe I 6-104 Me SO₂Me I 6-105 Me SEt Cl 6-106 Me SOEt Cl 6-107 Me SO₂Et Cl 6-108 Me SEt Br 6-109 Me SOEt Br 6-110 Me SO₂Et Br 6-111 Me SEt I 6-112 Me SOEt I 6-113 Me SO₂Et I 6-114 Me SEt F 6-115 Me SOEt F 6-116 Me SO₂Et F 6-117 Cl OCH₂(CO)NMe₂ Cl 6-118 Cl Cl SO₂Me 6-119 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.05 (d, 2H), 7.78 (d, 1H), 5.30 (s, 2H), 4.04 (q, 2H), 3.20 (s, 3H), 1.49 (s, 9H) 6-120 Cl 5-cyanomethyl-4,5- SO₂Et ¹H-NMR, CDCl₃, 400 MHz dihydro-1,2-oxazol-3- 8.10 (d, 1H), 7.94 (bs, 2H), 5.15 (m, yl 1H), 3.73 (m, 1H), 3.35 (m, 2H), 3.25 (m, 1H), 2.90 (m, 2H), 1.48 (s, 9H), 1.28 (t, 3H) 6-121 Cl CH₂O-tetra- SO₂Me hydrofuran-3-yl 6-122 Cl CH₂O-tetra- SO₂Me hydrofuran-2-yl 6-123 Cl SMe SO₂Me 6-124 Cl F SMe 6-125 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-126 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 6-127 Cl O(CH₂)-5-pyrrolidin- Cl 2-one 6-128 Cl SMe Cl 6-129 Cl S(O)Me SO₂Me 6-130 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 6-131 Cl O(CH₂)₂OMe Cl 6-132 Cl O(CH₂)₂OMe SO₂Me 6-133 Cl O(CH₂)₄OMe SO₂Me 6-134 Cl O(CH₂)₄OMe SO₂Et 6-135 Cl O(CH₂)₃OMe SO₂Me 6-136 Cl O(CH₂)₃OMe SO₂Et 6-137 Cl O(CH₂)₂OMe SO₂Me 6-138 Cl O(CH₂)₂OMe SO₂Et 6-139 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 6-140 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 6-141 Cl SO₂Me Me 6-142 Cl SEt Me 6-143 Cl SOEt Me 6-144 Cl SO₂Et Me 6-145 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 6-146 Cl Cl SO₂Me 6-147 F SMe CF₃ 6-148 F S(O)Me CF₃ 6-149 OMe SMe CF₃ 6-150 OMe S(O)Me CF₃ 6-151 OMe SO₂Me CF₃ 6-152 Et NH(CH₂)₂OMe SO₂Me 6-153 Et F SO₂Me 6-154 Et SMe CF₃ 6-155 CF₃ F SO₂Me 6-156 CF₃ F SO₂Et 6-157 CF₃ O(CH₂)₂OMe SO₂Et 6-158 CF₃ O(CH₂)₃OMe SO₂Et 6-159 CF₃ O(CH₂)₂OMe SO₂Me 6-160 CF₃ O(CH₂)₃OMe SO₂Me 6-161 CF₃ OCH₂CONMe₂ SO₂Me 6-162 CF₃ OCH₂CONMe₂ SO₂Et 6-163 CF₃ OCH₂CONMe₂ Cl 6-164 CF₃ OCH₂CONMe₂ Br 6-165 CF₃ OCH₂CONMe₂ I 6-166 CF₃ OCH₂CONMe₂ F 6-167 CF₃ O(CH₂)₂OMe Cl 6-168 CF₃ O(CH₂)₃OMe Cl 6-169 CF₃ O(CH₂)₂OMe Br 6-170 CF₃ O(CH₂)₃OMe Br 6-171 CF₃ O(CH₂)₂OMe I 6-172 CF₃ O(CH₂)₃OMe I 6-173 CF₃ O(CH₂)₂OMe F 6-174 CF₃ O(CH₂)₃OMe F 6-175 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 6-176 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 6-177 CF₃ [1,4]dioxan-2-yl- Cl methoxy 6-178 CF₃ [1,4]dioxan-2-yl- Br methoxy 6-179 CF₃ [1,4]dioxan-2-yl- I methoxy 6-180 CF₃ [1,4]dioxan-2-yl- F methoxy 6-181 Br OMe Br 6-182 Br O(CH₂)₂OMe Br 6-183 Br O(CH₂)₄OMe SO₂Me 6-184 Br O(CH₂)₄OMe SO₂Et 6-185 Br O(CH₂)₃OMe SO₂Me 6-186 Br O(CH₂)₃OMe SO₂Et 6-187 Br O(CH₂)₂OMe SO₂Me 6-188 Br O(CH₂)₂OMe SO₂Et 6-189 Br [1,4]dioxan-2-yl- SO₂Me methoxy 6-190 Br [1,4]dioxan-2-yl- SO₂Et methoxy 6-191 Br SMe Me 6-192 Br SOMe Me 6-193 Br SO₂Me Me 6-194 Br SEt Me 6-195 Br SOEt Me 6-196 Br SO₂Et Me 6-197 I O(CH₂)₄OMe SO₂Me 6-198 I O(CH₂)₄OMe SO₂Et 6-199 I O(CH₂)₃OMe SO₂Me 6-200 I O(CH₂)₃OMe SO₂Et 6-201 I O(CH₂)₂OMe SO₂Me 6-202 I O(CH₂)₂OMe SO₂Et 6-203 I [1,4]dioxan-2-yl- SO₂Me methoxy 6-204 I [1,4]dioxan-2-yl- SO₂Et methoxy 6-205 I SMe Me 6-206 I SOMe Me 6-207 I SO₂Me Me 6-208 I SEt Me 6-209 I SOEt Me 6-210 I SO₂Et Me 6-211 CH₂SMe OMe SO₂Me 6-212 CH₂OMe OMe SO₂Me 6-213 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 6-214 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 6-215 CH₂O(CH₂)₃OMe OMe SO₂Me 6-216 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 6-217 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 6-218 SO₂Me NH₂ CF₃ 6-219 SO₂Me F CF₃ 6-220 SO₂Me NHEt Cl 6-221 SMe SEt F 6-222 SMe SMe F 6-223 Me NH₂ Cl 6-224 Me NH₂ Br 6-225 Me NHMe Cl 6-226 Me NHMe Br 6-227 Me NMe₂ Cl 6-228 Me NMe₂ Br 6-229 NO₂ O(CH₂)₂OMe Me 6-230 CF₃ S(O)₂Et SO₂Me 6-231 CF₃ S(O)₂Et SO₂Et 6-232 CF₃ SCH₂CONMe₂ SO₂Me 6-233 CF₃ SCH₂CONMe₂ SO₂Et 6-234 CF₃ SCH₂COOH SO₂Me 6-235 CF₃ SCH₂COOH SO₂Et 6-236 Me SO₂—CH₂—CH₂—CH═CH₂ CF₃ 6-237 Cl Me SO₂Et 6-238 CF₃ Set SO₂Me 6-239 OMe NO₂ Cl 6-240 OMe NH(CO)i-Pr Cl 6-241 OMe NH(CO)CH₂Ph Cl 6-242 CF₃ SEt SO₂Et 6-243 CF₃ S(O)Et SO₂Me 6-244 Cl Me Cl 6-245 Me 3,5-dimethylpyrazol-6-yl SO₂Me 6-246 SMe H CF₃ 6-247 Me 1,2,3-triazol-6-yl SO₂Me 6-248 Me Me SMe 6-249 Me pyrrolidin-2-on-6-yl SO₂Me 6-250 CF₃ S(O)Et SO₂Et 6-251 Cl pyrazol-6-yl SO₂Me 6-252 Me 3-methylpyrazol-6-yl SO₂Me 6-253 Cl CH₂—N(Et)OMe SO₂Me 6-254 Me Me Cl 6-255 OH Cl Cl 6-256 Me 1,2,4-triazol-1-yl SO₂Me 6-257 Me 4-methoxypyrazol-6-yl SO₂Me 6-258 Me 1,2,4-triazol-1-yl CF₃ 6-259 Me tetrahydropyrimidin- SO₂Me 2(1H)-on-6-yl 6-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me 6-261 Me NH—iPr SO₂Me 6-262 Cl NH—CH₂—(CO)NHEt Cl 6-263 Me NH—CH₂—(CO)NMe₂ SO₂Me 6-264 Me NH—CH₂-furan-₂-yl SO₂Me 6-265 Me NH—CH₂—(CO)NHEt SO₂Me 6-266 Me F SO₂Me 6-267 F SO₂Me SO₂Me 6-268 Cl (4-cyclopropyl-3- Cl methyl-5-oxo-4, 5- dihydro-1H-1,2,4- triazol-6-yl)methyl 6-269 Cl [4-methyl-5-oxo-3- Cl (2,2,2-trifluoro- ethoxy)-4,5-dihydro- 1H-1,2,4-triazol-6-yl]- methyl 6-270 Cl (3-isopropoxy-4- Cl methyl-5-oxo-4, 5- dihydro-1H-1,2,4- triazol-6-yl]methyl 6-271 Cl (4-methyl-5-oxo-4,5- Cl dihydro-1H-1,2,4- triazol-6-yl)methyl 6-272 Me Cl SO₂Et 6-273 SO₂Me F Cl 6-274 Cl morpholin- 4-yl 6-275 Me isobutyl(methyl)- SO₂Me carbamoylamino 6-276 Me 3-oxomorpholin-4-yl SO₂Me 6-277 OMe [ethyl(methylsulfonyl) Cl amino]methyl 6-278 Cl (4-methyl-3- trifluoro- methyl-5- oxo-4,5- dihydro-1H- 1,2,4- triazol-6-yl)- 6-279 OMe benzoylamino Cl 6-280 OMe cyclopropylcarbonyl- Cl amino 6-281 OMe propionylamino Cl 6-282 NO₂ SO₂Me SO₂Me ¹H NMR, MeOD, 400 MHz 8.66 (d, 1H), 8.38 (d, 1H), 3.69 (s, 3H), 3.60 (s, 3H), 1.45 (s, 9H) 6-283 NO₂ SOMe SO₂Me ¹H NMR, MeOD, 400 MHz 8.36 (d, 1H), 8.25 (d, 1H), 3.41 (s, 3H), 3.40 (s, 3H), 1.42 (s, 9H) 6-284 NO₂ SO₂Me Cl ¹H NMR, MeOD, 400 MHz 8.15 (d, 1H), 8.03 (d, 1H), 3.48 (s, 3H), 1.45 (s, 9H) 6-285 NO₂ SOMe Br ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1H), 8.2 (d, 1H), 7.95 (d, 1H), 3.18 (s, 3H), 1.38 (s, 9H) 6-286 NO₂ SOMe Cl ¹H NMR, MeOD, 400 MHz 8.02 (d, 1H), 7.92 (d, 1H), 3.28 (s, 3H), 1.45 (s, 9H) 6-287 NO₂ SMe SO₂Me ¹H NMR, MeOD, 400 MHz 8.51 (d, 1H), 8.2 (d, 1H), 3.55 (s, 3H), 2.6 (s, 3H), 1.43 (s, 9H) 6-288 NO₂ SMe Br ¹H NMR, DMSO-d₆, 400 MHz 11.25 (s, 1H), 8.25 (d, 1H), 7.92 (d, 1H), 2.45 (s, 3H), 1.35 (s, 9H) 6-289 NO₂ SMe Cl ¹H NMR, CDCl₃, 400 MHz 7.75 (s, 2H), 2.48 (s, 3H), 1.42 (s, 9H) 6-290 Cl CH₂OEt SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.03 (d, 1H), 7.85 (s, 1H), 7.78 (d, 1H), 5.08 (s, 2H), 3.69 (q, 2H), 3.4 (q, 2H), 1.48 (s, 9H), 1.25 (t, 3H), 1.24 (t, 3H) 6-291 Cl CH₂OC₂H₄OC₂H₄OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.08 (d, 1H), 7.96 (s, 1H), 7.75 (d, 1H), 5.19 (s, 2H), 3.82 (dd, 2H), 3.68 (dd, 2H), 3.58 (dd, 2H), 3.48 (dd, 2H), 3.31 (s, 3H), 3.29 (s, 3H), 1.49 (s, 9H) 6-292 Cl CH₂OMe SO₂Et ¹H NMR, CDCl₃, 400 MHz 8.01 (d, 1H), 7.92 (s, 1H), 7.77 (d, 1H), 5.03 (s, 2H), 3.5 (s, 3H), 3.38 (q, 2H), 1.48 (s, 9H), 1.22 (t, 3H) 6-293 Cl 5-methoxymethyl-5- SO₂Et ¹H NMR, CDCl₃, 400 MHz methyl-4,5-dihydro- 8.09 (d, 1H), 7.91 (d, 1H), 7.82 (s, 1,2-oxazol-3-yl 1H), 3.53 (q, 2H), 3.48 (d, 1H), 3.45 (s, 3H), 3.4 (q, 2H), 3,09 (d, 1H), 1.55 (s, 3H), 1.48 (s, 9H), 1.28 (t, 3H) 6-294 Cl 5-methoxymethyl-4,5- SO₂Et ¹H NMR, CDCl₃, 400 MHz dihydro-1,2-oxazol-3- 8.09 (d, 1H), 7.91 (d, 1H), 7.89 (s, yl 1H), 5.05 (m, 1H), 3.69 (dd, 1H), 3.6 (dd, 1H), 3.47 (dd, 1H), 3.45 (s, 3H), 3.38 (q, 2H), 3.25 (dd, 1H), 1.48 (s, 9H), 1.28 (t, 3H) 6-295 Et SOMe CF₃ ¹H NMR, CDCl₃, 400 MHz 8.4 (s, br, 1H), 7.69 (d, 1H), 7.62 (d, 1H), 3.48 (q, 2H), 3.0 (s, 3H), 1.48 (s, 9H), 1.28 (t, 3H) 6-296 Cl 5-ethoxymethyl-4,5- SO₂Et ¹H NMR, CDCl₃, 400 MHz dihydro-1,2-oxazol-3- 8.12 (d, 1H), 7.95 (d, 1H), 7.75 (s, yl 1H), 5.05 (m, 1H), 3.73 (dd, 1H), 3.65 (dd, 1H), 3.62 (q, 2H), 3.5 (dd, 1H), 3.38 (q, 2H), 3.29 (dd, 1H), 1.48 (s, 9H), 1.29 (t, 3H), 1.22 (t, 3H) 6-308 Cl NMe₂ Cl 6-309 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 6-313 Me SO₂(CH₂)₂OMe CF₃ 6-314 Me SOEt SO₂Me 6-315 Me SO₂Et SO₂Me 6-316 Me SMe 1,2,4- triazol-1-yl 6-317 OEt SMe CF₃ 6-318 Me S(CH₂)₂OMe CF₃ 6-319 Me SOMe 1,2,4- triazol-1-yl 6-320 OEt SOMe CF₃ 6-321 Me SO(CH₂)₂OMe CF₃ 6-322 Me SCH₂CCMe SO₂Me 6-323 Me S—c-Pen SO₂Me 6-324 OMe SMe OMe 6-325 Me SCH₂CH═CHCH₃ SO₂Me 6-326 Me SOCH₂CCMe SO₂Me 6-327 Me SO₂—c-Pen SO₂Me 6-328 Me SO—c-Pen SO₂Me 6-329 Me S(CH₂)₃Cl SO₂Me 6-330 Me SCH₂(4-F—Ph) SO₂Me 6-331 Me SO₂CH₂CCMe SO₂Me 6-332 Me SO₂CH₂CH═CHCH₃ SO₂Me 6-333 Me SOCH₂CH═CHCH₃ SO₂Me 6-334 Me SOCH₂-epoxy-CH₃ SO₂Me 6-335 Me SO₂(CH₂)₃C1 SO₂Me 6-336 Me SO(CH₂)₃Cl SO₂Me 6-337 Me SOCH₂(4-F—Ph) SO₂Me 6-338 Me SO₂CH₂(4-F—Ph) SO₂Me 6-339 Me SO₂Me C₂F₅ 6-340 O(CH₂)₂OMe SMe CF₃ 6-341 O(CH₂)₂OMe SO₂Me CF₃ 6-342 O(CH₂)₂OMe SOMe CF₃ 6-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me 6-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me 6-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me 6-346 OEt SEt CF₃ 6-347 O—CH₂—c-Pr SMe CF₃ 6-348 OMe SEt CF₃ 6-349 OMe SO₂Et CF₃ 6-350 OMe SOEt CF₃ 6-351 OEt SO₂Et CF₃ 6-352 OEt SOEt CF₃ 6-353 O—CH₂—c-Pr SOMe CF₃ 6-354 O—CH₂—c-Pr SO₂Me CF₃ 6-355 Me SEt SO₂Me

TABLE 7 Compounds of the general formula (I) according to the invention in which R is trifluoromethyl

No. X Y Z Physical data 7-1 CF₃ OCH₂CON(Me)Et SO₂Me 7-2 CF₃ OCH₂CON(Me)Et SO₂Et 7-4 CF₃ 2-(1H-pyrazol-1- SO₂Me yl)ethoxyl 7-5 CF₃ 2-(1H-pyrazol-1- SO₂Et yl)ethoxyl 7-6 CF₃ tetrahydrofuran-2-yl- SO₂Me methoxy 7-7 CF₃ tetrahydrofuran-2-yl- SO₂Et methoxy 7-8 CF₃ OH SO₂Me 7-9 CF₃ OH SO₂Et 7-10 CF₃ SH SO₂Me 7-11 CF₃ SH SO₂Et 7-15 CF₃ SMe SO₂Me 7-16 CF₃ SMe SO₂Et 7-17 CF₃ S(O)Me SO₂Me 7-24 CF₃ S(O)Me SO₂Et 7-25 CF₃ S(O)₂Me SO₂Me 7-26 CF₃ S(O)₂Me SO₂Et 7-27 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethoxy 7-28 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethyl}sulfanyl 7-29 CF₃ 2-[(methylsulfonyl)- SO₂Et amino]ethyl}sulfanyl 7-30 NO₂ O(CH₂)₂OMe OMe 7-31 NO₂ OMe Me 7-32 NO₂ NH₂ OMe 7-33 NO₂ NH₂ SO₂Et 7-34 NO₂ NH₂ Cl 7-35 NO₂ NHMe Cl 7-36 NO₂ NMe₂ Cl 7-37 NO₂ NH₂ Br 7-38 NO₂ NHMe Br 7-39 NO₂ NMe₂ Br 7-40 NO₂ NH₂ F 7-41 NO₂ NHMe F 7-42 NO₂ NMe₂ F 7-43 NO₂ NH₂ SO₂Me 7-44 NO₂ NHMe SO₂Me 7-45 NO₂ NMe₂ SO₂Me 7-46 NO₂ NH₂ 1H-1,2,4- triazol-1-yl 7-47 NO₂ NHMe 1H-1,2,4- triazol-1-yl 7-48 NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 7-49 Me F F ¹H NMR, DMSO-d₆, 400 MHz 11.26 (s, 1H), 7.49 (m, 2H), 2.8 (q, 2H), 2.38 (s, 3H), 1.25 (t, 3H) 7-50 Me F Cl ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1H), 7.61 (t, 1H), 7.48 (d, 1H), 2.79 (q, 2H), 2.35 (s, 1H), 1.26 (t, 3H) 7-51 Me SMe CF₃ 7-52 Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.45 (s, 1H), 8.05 (d, 1H), 7.79 (d, 1H), 3.44 (s, 3H), 2.80 (q, 2H), 2.48 (s, 3H), 1.28 (t, 3H) 7-53 Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 8.27 (d, 1H), 8.08 (d, 1H), 3.60 (s, 3H), 3.58 (s, 3H), 2.81 (q, 2H), 2.71 (s, 3H), 1.27 (t, 3H) 7-54 Me SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.05 (bs, 1H), 7.88 (d, 1H), 7.78 (d, 1H), 3.20 (s, 3H), 2.90 (q, 2H), 2.75 (s, 3H), 1.40 (t, 3H) 7-55 Me Cl CF₃ 7-56 Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.44 (s, 1H), 7.88 (m, 2H), 3.05 (s, 3H), 2.87 (s, 3H), 2.82 (q, 2H), 1.28 (t, 3H) 7-57 Me SEt OMe 7-58 Me NMe₂ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1H), 7.88 (d, 1H), 7.60 (d, 1H), 3.31 (s, 3H), 2.84 (s, 6H), 2.80 (q, 2H), 2.39 (s, 3H), 1.28 (t, 3H) 7-59 Me NH(CH₂)₂OMe SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.84 (bs, 1H), 7.52 (d, 1H), 7.09 (d, 1H), 5.68 (bs, 1H), 3.57 (m, 2H), 3.35 (m, 5H), 3.13 (s, 3H), 2.90 (q, 2H), 2.37 (s, 3H), 1.40 (t, 3H) 7-60 Me O(CH₂)₄OMe SO₂Me 7-61 Me NH₂ SO₂Me 7-62 Me O(CH₂)₂—O(3,5-di- SO₂Me methoxypyrimidin-2-yl 7-63 Me O(CH₂)₂—O—NMe₂ Cl 7-64 Me O(CH₂)₂—NH(CO)NMe₂ Cl 7-65 Me O(CH₂)-5-pyrrolidin-2- Br one 7-66 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 7-67 Me O(CH₂)—(CO)NEt₂ Br 7-68 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one 7-69 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 7-70 Me O(CH₂)₂—NHCO₂Me Cl 7-71 Me 4,5-dihydro-1,2-oxazol- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 3-yl 11.46 (s, 1H), 8.04 (d, 1H), 7.90 (d, 1H), 4.50 (t, 2H), 3.35 (t, 2H), 3.27 (s, 3H), 2.82 (q, 2H), 2.35 (s, 3H), 1.27 (t, 3H) 7-72 Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.34 (s, 1H), 7.92 (d, 1H), 7.59 (d, 1H), 3.27 (s, 3H), 2.80 (q, 2H), 2.66 (s, 3H), 2.36 (s, 3H), 1.27 (t, 3H) 7-73 Me OH SO₂Me 7-74 Me O—CH₂—NHSO₂cPr Cl 7-75 Me O(CH₂)₂NHSO₂Me SO₂Me 7-76 Me S(O)Me SO₂Me 7-77 Me SMe SO₂Me 7-78 Me SMe OMe 7-79 Me S(O)Me OMe 7-80 Me SO₂Me OMe 7-81 Me SMe Cl 7-82 Me S(O)Me Cl 7-83 Me SO₂Me Cl 7-84 Me [1,4]dioxan-2-yl- SO₂Me methoxy 7-85 Me [1,4]dioxan-2-yl- SO₂Et methoxy 7-86 Me O(CH₂)₄OMe SO₂Et 7-87 Me O(CH₂)₃OMe SO₂Me 7-88 Me O(CH₂)₃OMe SO₂Et 7-89 Me O(CH₂)₂OMe SO₂Me 7-90 Me O(CH₂)₂OMe SO₂Et 7-91 Me S(O)Me SO₂Me 7-92 Me SMe SO₂Me 7-93 Me SMe OMe 7-94 Me S(O)Me OMe 7-95 Me SO₂Me OMe 7-96 Me SMe Cl 7-97 Me S(O)Me Cl 7-98 Me SO₂Me Cl 7-99 Me SMe Br 7-100 Me SOMe Br 7-101 Me SO₂Me Br 7-102 Me SMe I 7-103 Me SOMe I 7-104 Me SO₂Me I 7-105 Me SEt Cl 7-106 Me SOEt Cl 7-107 Me SO₂Et Cl 7-108 Me SEt Br 7-109 Me SOEt Br 7-110 Me SO₂Et Br 7-111 Me SEt I 7-112 Me SOEt I 7-113 Me SO₂Et I 7-114 Me SEt F 7-115 Me SOEt F 7-116 Me SO₂Et F 7-117 Cl OCH₂(CO)NMe₂ Cl ¹H NMR, DMSO-d₆, 400 MHz 11.44 (s, 1H), 7.65 (d, 1H), 7.49 (d, 1H), 4.74 (s, 2H), 3.02 (s, 3H), 2.87 (s, 3H), 2.81 (q, 2H), 1.27 (t, 3H) 7-118 Cl Cl SO₂Me 7-119 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.60 (s, 1H), 8.12 (d, 1H), 7.98 (d, 1H), 5.27 (s, 2H), 4.30 (q, 2H), 3.38 (s, 3H), 2.83 (q, 2H), 1.30 (t, 3H) 7-120 Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz dihydro-1,2-oxazol-3-yl 11.62 (s, 1H), 8.11 (m, 2H), 5.20 (m, 1H), 3.60 (m, 1H), 3.44 (q, 2H), 3.15 (m, 1H), 3.02 (m, 2H), 2.81 (q, 2H), 1.28 (t, 3H), 1.16 (t, 3H) 7-121 Cl CH₂O-tetrahydrofuran- SO₂Me ¹H NMR, CDCl₃, 400 MHz 3-yl 8.70 (bs, 1H), 7.94 (d, 1H), 7.72 (d, 1H), 5.06 (m, 2H), 4.35 (m, 1H), 3.73-3.92 (m, 4H), 3.36 (q, 2H), 2.92 (q, 2H), 2.10 (m, 2H), 1.40 (t, 3H), 1.22 (t, 3H) 7-122 Cl CH₂O-tetrahydrofuran- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 2-yl 11.55 (s, 1H), 8.14 (d, 1H), 7.93 (d, 1H), 3.58 (s, 3H), 2.81 (q, 2H), 2.48 (s, 3H), 1.28 (t, 3H), 7-123 Cl SMe SO₂Me 7-124 Cl F SMe 7-125 Cl CH₂OCH₂- SO₂Me ¹H NMR, CDCl₃, 400 MHz tetrahydrofuran-2-yl 8.84 (bs, 1H), 8.0 (d, 1H), 7.70 (d, 1H), 5.12 (s, 2H), 4.05 (m, 1H), 3.55-3.80 (m, 4H), 3.28 (s, 3H), 2.90 (q, 2H), 1.78-2.0 (m, 3H), 1.48-1.59 (m, 1H), 1.40 (t, 3H) 7-126 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 7-127 Cl O(CH₂)-5-pyrrolidin-2- Cl one 7-128 Cl SMe Cl ¹H NMR, DMSO-d₆, 400 MHz 11.41 (s, 1H), 7.22 (d, 1H), 7.68 (d, 1H), 2.80 (q, 2H), 2.43 (s, 3H), 1.28 (t, 3H) 7-129 Cl S(O)Me SO₂Me 7-130 Cl CH₂O-tetrahydrofuran- SO₂Et 3-yl 7-131 Cl O(CH₂)₂OMe Cl 7-132 Cl O(CH₂)₂OMe SO₂Me 7-133 Cl O(CH₂)₄OMe SO₂Me 7-134 Cl O(CH₂)₄OMe SO₂Et 7-135 Cl O(CH₂)₃OMe SO₂Me 7-136 Cl O(CH₂)₃OMe SO₂Et 7-137 Cl O(CH₂)₂OMe SO₂Me 7-138 Cl O(CH₂)₂OMe SO₂Et 7-139 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 7-140 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 7-141 Cl SO₂Me Me 7-142 Cl SEt Me 7-143 Cl SOEt Me 7-144 Cl SO₂Et Me 2-145 Cl 4,5-dihydro-1,7-oxazol- SO₂Me 3-yl 7-146 Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.6 (s, 1H), 8.16 (d, 1H), 7.94 (d, 1H), 3.49 (s, 3H), 3.82 (q, 2H), 1.28 (t, 3H) 7-147 F SMe CF₃ 7-148 F S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.75 (bs, 1H), 8.14 (dd, 1H), 7.90 (d, 1 H), 2.81 (q, 2H), 1.78-2.0 (m, 3H), 1.28 (t, 3H) 7-149 OMe SMe CF₃ 7-150 OMe S(O)Me CF₃ 7-151 OMe SO₂Me CF₃ 7-152 Et NH(CH₂)₂OMe SO₂Me 7-153 Et F SO₂Me 7-154 Et SMe CF₃ 7-155 CF₃ F SO₂Me 7-156 CF₃ F SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.68 (s, 1H), 8.3 (t, 1H), 7.89 (d, 1H), 3.49 (s, 3H), 2.79 (q, 2H), 1.27 (t, 3H) 7-157 CF₃ O(CH₂)₂OMe SO₂Et 7-158 CF₃ O(CH₂)₃OMe SO₂Et 7-159 CF₃ O(CH₂)₂OMe SO₂Me 7-160 CF₃ O(CH₂)₃OMe SO₂Me 7-161 CF₃ OCH₂CONMe₂ SO₂Me 7-162 CF₃ OCH₂CONMe₂ SO₂Et 7-163 CF₃ OCH₂CONMe₂ Cl 7-164 CF₃ OCH₂CONMe₂ Br 7-165 CF₃ OCH₂CONMe₂ I 7-166 CF₃ OCH₂CONMe₂ F 7-167 CF₃ O(CH₂)₂OMe Cl 7-168 CF₃ O(CH₂)₃OMe Cl 7-169 CF₃ O(CH₂)₂OMe Br 7-170 CF₃ O(CH₂)₃OMe Br 7-171 CF₃ O(CH₂)₂OMe I 7-172 CF₃ O(CH₂)₃OMe I 7-173 CF₃ O(CH₂)₂OMe F 7-174 CF₃ O(CH₂)₃OMe F 7-175 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 7-176 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 7-177 CF₃ [1,4]dioxan-2-yl- Cl methoxy 2-178 CF₃ [1,4]dioxan-2-yl- Br methoxy 7-179 CF₃ [1,4]dioxan-2-yl- I methoxy 7-180 CF₃ [1,4]dDioxan-2-yl- F methoxy 7-181 Br OMe Br 7-182 Br O(CH₂)₂OMe Br 7-183 Br O(CH₂)₄OMe SO₂Me 7-184 Br O(CH₂)₄OMe SO₂Et 7-185 Br O(CH₂)₃OMe SO₂Me 7-186 Br O(CH₂)₃OMe SO₂Et 7-187 Br O(CH₂)₂OMe SO₂Me 7-188 Br O(CH₂)₂OMe SO₂Et 7-189 Br [1,4]dioxan-2-yl- SO₂Me methoxy 7-190 Br [1,4]dioxan-2-yl- SO₂Et methoxy 7-191 Br SMe Me 7-192 Br SOMe Me 7-193 Br SO₂Me Me 7-194 Br SEt Me 7-195 Br SOEt Me 7-196 Br SO₂Et Me 7-197 I O(CH₂)₄OMe SO₂Me 7-198 I O(CH₂)₄OMe SO₂Et 7-199 I O(CH₂)₃OMe SO₂Me 7-200 I O(CH₂)₃OMe SO₂Et 7-201 I O(CH₂)₂OMe SO₂Me 7-202 I O(CH₂)₂OMe SO₂Et 7-203 I [1,4]dioxan-2-yl- SO₂Me methoxy 7-204 I [1,4]dioxan-2-yl- SO₂Et methoxy 7-205 I SMe Me 7-206 I SOMe Me 7-207 I SO₂Me Me 7-208 I SEt Me 7-209 I SOEt Me 7-210 I SO₂Et Me 7-211 CH₂SMe OMe SO₂Me 7-212 CH₂OMe OMe SO₂Me 7-213 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 7-214 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 7-215 CH₂O(CH₂)₃OMe OMe SO₂Me 7-216 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 7-217 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 7-218 SO₂Me NH₂ CF₃ 7-219 SO₂Me F CF₃ 7-220 SO₂Me NHEt Cl 7-221 SMe SEt F 7-222 SMe SMe F 7-223 Me NH₂ Cl 7-224 Me NH₂ Br 7-225 Me NHMe Cl 7-226 Me NHMe Br 7-227 Me NMe₂ Cl 7-228 Me NMe₂ Br 7-227 Me NMe₂ Cl 7-228 Me NMe₂ Br 7-229 NO₂ O(CH₂)₂OMe Me 7-230 CF₃ S(O)₂Et SO₂Me 7-231 CF₃ S(O)₂Et SO₂Et 7-232 CF₃ SCH₂CONMe₂ SO₂Me 7-233 CF₃ SCH₂CONMe₂ SO₂Et 7-234 CF₃ SCH₂COOH SO₂Me 7-235 CF₃ SCH₂COOH SO₂Et 7-236 Me SO₂—CH₂—CH₂—CH═CH₂ CF₃ 7-237 Cl Me SO₂Et 7-238 CF₃ SEt SO₂Me 7-239 OMe NO₂ Cl 7-240 OMe NH(CO)i-Pr Cl 7-241 OMe NH(CO)CH₂Ph Cl 7-242 CF₃ SEt SO₂Et 7-243 CF₃ S(O)Et SO₂Me 7-244 Cl Me Cl 7-245 Me 3,5-dimethylpyrazol-1-yl SO₂Me 7-247 Me 1,2,3-triazol-1-yl SO₂Me 7-248 Me Me SMe 7-249 Me pyrrolidin-2-on-1-yl SO₂Me 7-250 CF₃ S(O)Et SO₂Et 7-251 Cl pyrazol-1-yl SO₂Me 7-252 Me 3-methylpyrazol-1-yl SO₂Me 7-253 Cl CH₂—N(Et)OMe SO₂Me 7-254 Me Me Cl 7-255 OH Cl Cl 7-256 Me 1,2,4-triazol-1-yl SO₂Me 7-257 Me 4-methoxypyrazol-1-yl SO₂Me 7-258 Me 1,2,4-triazol-1-yl CF₃ 7-259 Me tetrahydropyrimidin- SO₂Me 2(1H)-on-1-yl 7-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me 7-261 Me NH—iPr SO₂Me 7-262 Cl NH—CH₂—(CO)NHEt Cl 7-263 Me NH—CH₂—(CO)NMe₂ SO₂Me 7-264 Me NH—CH₂-furan-2-yl SO₂Me 7-265 Me NH—CH₂—(CO)NHEt SO₂Me 7-266 Me F SO₂Me 7-267 F SO₂Me SO₂Me 7-268 Cl (4-cyclopropyl-3- Cl methyl-5-oxo-4, 5- dihydro-1H-1,2,4- triazol-1-yl)methyl 7-269 Cl [4-methyl-5-oxo-3- Cl (2,2,2-trifluoroethoxy)- 4,5-dihydro-1H-1,2,4- triazol-1-yl]methyl 7-270 Cl (3-isopropoxy-4-methyl- Cl 5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1-yl]- methyl 7-271 Cl (4-methyl-5-oxo-4,5- Cl dihydro-1H-1,2,4- triazol-1-yl)methyl 7-272 Me Cl SO₂Et 7-273 SO₂Me F Cl 7-274 Me 1,2,3-triazol-1-yl SO₂Me 7-275 Me isobutyl(methyl)- SO₂Me carbamoylamino 7-276 Me 3-oxomorpholin-4-yl SO₂Me 7-277 OMe [ethyl(methylsulfonyl)- Cl amino]methyl 7-278 F SO₂Me CF₃ 7-279 OMe benzoylamino Cl 7-280 OMe cyclopropylcarbonyl- Cl amino 7-281 OMe propionylamino Cl 7-282 NO₂ SO₂Me SO₂Me 7-283 NO₂ SO₂Me Cl 7-284 NO₂ SOMe SO₂Me 7-285 NO₂ SOMe Br 7-286 NO₂ SOMe Cl 7-287 NO₂ SMe SO₂Me 7-288 NO₂ SMe Br 7-289 NO₂ SMe Cl 7-290 Cl CH₂OCH(CH₃)₂ SO₂Et 7-291 Cl CH₂OEt SO₂Et 7-292 Cl CH₂OMe SO₂Et 7-293 Cl CH₂OCH₂C₂F₅ SO₂Me 7-294 Cl CH₂OCH₂CHF₂ SO₂Me 7-295 Cl CH₂OCH₂CCH SO₂Et 7-296 Cl CH₂OC₂H₄OMe SO₂Me 7-297 Cl CH₂(OC₂H₄)₂OMe SO₂Me 7-298 Cl 5-ethoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 7-299 Cl 5-methoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 7-300 Et SOMe CF₃ 7-301 iPr SMe CF₃ 7-302 Et SMe CF₃ 7-303 Et SO₂Me CF₃ 7-304 cPr SOMe CF₃ 7-305 CH═CH₂ SMe CF₃ 7-306 Et SMe Cl 7-307 Et SO₂Me Cl 7-308 Cl NMe₂ Cl 7-309 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 7-313 Me SO₂(CH₂)₂OMe CF₃ 7-314 Me SOEt SO₂Me 7-315 Me SO₂Et SO₂Me 7-316 Me SMe 1,2,4- triazol-1-yl 7-317 OEt SMe CF₃ 7-318 Me S(CH₂)₂OMe CF₃ 7-319 Me SOMe 1,2,4- triazol-1-yl 7-320 OEt SOMe CF₃ 7-321 Me SO(CH₂)₂OMe CF₃ 7-322 Me SCH₂CCMe SO₂Me 7-323 Me S—c-Pen SO₂Me 7-324 OMe SMe OMe 7-325 Me SCH₂CH═CHCH₃ SO₂Me 7-326 Me SOCH₂CCMe SO₂Me 7-327 Me SO₇₋c-Pen SO₂Me 7-328 Me SO—c-Pen SO₂Me 7-329 Me S(CH₂)₃Cl SO₂Me 7-330 Me SCH₂(4-F—Ph) SO₂Me 7-331 Me SO₂CH₂CCMe SO₂Me 7-332 Me SO₂CH₂CH═CHCH₃ SO₂Me 7-333 Me SOCH₂CH═CHCH₃ SO₂Me 7-334 Me SOCH₂-epoxy-Me SO₂Me 7-335 Me SO₂(CH₂)₃Cl SO₂Me 7-336 Me SO(CH₂)₃Cl SO₂Me 7-337 Me SOCH₂(4-F—Ph) SO₂Me 7-338 Me SO₂CH₂(4-F—Ph) SO₂Me 7-339 Me SO₂Me C₂F₅ 7-340 O(CH₂)₂OMe SMe CF₃ 7-341 O(CH₂)₂OMe SO₂Me CF₃ 7-342 O(CH₂)₂OMe SOMe CF₃ 7-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me 7-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me 7-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me 7-346 OEt SEt CF₃ 7-347 O—CH₂—c-Pr SMe CF₃ 7-348 OMe SEt CF₃ 7-349 OMe SO₂Et CF₃ 7-350 OMe SOEt CF₃ 7-351 OEt SO₂Et CF₃ 7-352 OEt SOEt CF₃ 7-353 O—CH₂—c-Pr SOMe CF₃ 7-354 O—CH₂—c-Pr SO₂Me CF₃ 7-355 Me SEt SO₂Me

TABLE 8 Compounds of the general formula (I) according to the invention in which R is cyano

No. X Y Z Physical data 8-1 CF₃ OCH₂CON(Me)Et SO₂Me 8-2 CF₃ OCH₂CON(Me)Et SO₂Et 8-4 CF₃ 2-(1H-pyrazol-1- SO₂Me yl)ethoxyl 8-5 CF₃ 2-(1H-pyrazol-1- SO₂Et yl)ethoxyl 8-6 CF₃ tetrahydrofuran-2-yl- SO₂Me methoxy 8-7 CF₃ tetrahydrofuran-2-yl- SO₂Et methoxy 8-8 CF₃ OH SO₂Me 8-9 CF₃ OH SO₂Et 8-10 CF₃ SH SO₂Me 8-11 CF₃ SH SO₂Et 8-15 CF₃ SMe SO₂Me 8-16 CF₃ SMe SO₂Et 8-17 CF₃ S(O)Me SO₂Me 8-24 CF₃ S(O)Me SO₂Et 8-25 CF₃ S(O)₂Me SO₂Me 8-26 CF₃ S(O)₂Me SO₂Et 8-27 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethoxy 8-28 CF₃ 2-[(methylsulfonyl)- SO₂Me amino]ethyl}sulfanyl 8-29 CF₃ 2-[(methylsulfonyl)- SO₂Et amino]ethyl}sulfanyl 8-30 NO₂ O(CH₂)₂OMe OMe 8-31 NO₂ OMe Me 8-32 NO₂ NH₂ OMe 8-33 NO₂ NH₂ SO₂Et 8-34 NO₂ NH₂ Cl 8-35 NO₂ NHMe Cl 8-36 NO₂ NMe₂ Cl 8-37 NO₂ NH₂ Br 8-38 NO₂ NHMe Br 8-39 NO₂ NMe₂ Br 8-40 NO₂ NH₂ F 8-41 NO₂ NHMe F 8-42 NO₂ NMe₂ F 8-43 NO₂ NH₂ SO₂Me 8-44 NO₂ NHMe SO₂Me 8-45 NO₂ NMe₂ SO₂Me 8-46 NO₂ NH₂ 1H-1,2,4- triazol-1-yl 8-47 NO₂ NHMe 1H-1,2,4- triazol-1-yl 8-48 NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 8-49 Me F F 8-50 Me F Cl 8-51 Me SMe CF₃ 8-52 Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.67 (s, 1H), 8.08 (d, 1H), 7.80 (d, 1H), 3.45 (s, 3H) 8-53 Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.68 (bs, 1H), 8.29 (d, 1H), 8.07 (d, 1H), 3.61 (s, 3H), 3.59 (s, 3H), 2.72 (s, 3H) 8-54 Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.64 (bs, 1H), 8.09 (d, 1H), 8.02 (d, 1H), 3.43 (s, 3H), 2.77 (s, 3H) 8-55 Me Cl CF₃ 8-56 Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.63 (s, 1H), 7.92 (d, 1H), 7.88 (d, 1H), 3.06 (s, 3H), 2.88 (s, 3H) 8-57 Me SEt OMe 8-58 Me NMe₂ SO₂Me 8-59 Me NH(CH₂)₂OMe SO₂Me 8-60 Me O(CH₂)₄OMe SO₂Me 8-61 Me NH₂ SO₂Me 8-62 Me O(CH₂)₂—O(3,5-di- SO₂Me methoxypyrimidin-2-yl 8-63 Me O(CH₂)₂—O—NMe₂ Cl 8-64 Me O(CH₂)₂—NH(CO)NMe₂ Cl 8-65 Me O(CH₂)-5-pyrrolidin-2- Br one 8-66 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 8-67 Me O(CH₂)—(CO)NEt₂ Br 8-68 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one 8-69 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 8-70 Me O(CH₂)₂—NHCO₂Me Cl 8-71 Me 4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 8-72 Me Me SO₂Me ¹H NMR, DMSO-d₆, 600 MHz 12.55 (s, 1H), 7.93 (d, 1H), 7.62 (d, 1H), 3.29 (s, 3H), 2.64 (s,3H), 2.38 (s,3H) 8-73 Me OH SO₂Me 8-74 Me O—CH₂—NHSO₂cPr Cl 8-75 Me O(CH₂)₂NHSO₂Me SO₂Me 8-76 Me S(O)Me SO₂Me 8-77 Me SMe SO₂Me 8-78 Me SMe OMe 8-79 Me S(O)Me OMe 8-80 Me SO₂Me OMe 8-81 Me SMe Cl 8-82 Me S(O)Me Cl 8-83 Me SO₂Me Cl 8-84 Me [1,4]dioxan-2-yl- SO₂Me methoxy 8-85 Me [1,4]dioxan-2-yl- SO₂Et methoxy 8-86 Me O(CH₂)₄OMe SO₂Et 8-87 Me O(CH₂)₃OMe SO₂Me 8-88 Me O(CH₂)₃OMe SO₂Et 8-89 Me O(CH₂)₂OMe SO₂Me 8-90 Me O(CH₂)₂OMe SO₂Et 8-91 Me S(O)Me SO₂Me 8-92 Me SMe SO₂Me 8-93 Me SMe OMe 8-94 Me S(O)Me OMe 8-95 Me SO₂Me OMe 8-96 Me SMe Cl 8-97 Me S(O)Me Cl 8-98 Me SO₂Me Cl 8-99 Me SMe Br 8-100 Me SOMe Br 8-101 Me SO₂Me Br 8-102 Me SMe I 8-103 Me SOMe I 8-104 Me SO₂Me I 8-105 Me SEt Cl 8-106 Me SOEt Cl 8-107 Me SO₂Et Cl 8-108 Me SEt Br 8-109 Me SOEt Br 8-110 Me SO₂Et Br 8-111 Me SEt I 8-112 Me SOEt I 8-113 Me SO₂Et I 8-114 Me SEt F 8-115 Me SOEt F 8-116 Me SO₂Et F 8-117 Cl OCH₂(CO)NMe₂ Cl 8-118 Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.82 (s, 1H), 8.21 (d, 1H), 7.92 (d, 1H), 3.50 (s, 3H) 8-119 Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.80 (s, 1H), 8.15 (d, 1H), 7.95 (d, 1H), 5.25 (s, 2H), 4.30 (q, 2H), 3.37 (s, 3H) 8-120 Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz dihydro-1,2-oxazol-3-yl 12.80 (s, 1H), 8.18 (d, 1H), 8.09 (d, 1H), 5.19 (m, 1H), 3.61 (m, 1H), 3.45 (q, 2H), 3.16 (m, 1H), 3.02 (m, 2H), 1.16 (t, 3H) 8-121 Cl CH₂O-tetrahydrofuran- SO₂Me 3-yl 8-122 Cl CH₂O-tetrahydrofuran- SO₂Me ¹H NMR, CDCl₃, 400 MHz 2-y1 10.92 (s, 1H), 7.78 (d, 1H), 7.70 (d, 1H), 5.0 (m, 2H), 4.32 (m, 1H), 3.70-3.88 (m, 4H), 3.36 (q, 2H), 2.06 (m, 2H), 1.22 (t, 3H) 8-123 Cl SMe SO₂Me 8-124 Cl F SMe 8-125 Cl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydrofuran-2-yl 12.78 (s, 1H), 8.16 (d, 1H), 7.92 (d, 1H), 5.11 (m, 2H), 3.99 (m, 1H), 3.71 (q, 1H), 3.63-3.54 (m, 3H), 3.39 (s, 3H), 1.95- 1.72 (m, 3H), 1.54 (m, 1H) 8-126 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 8-127 Cl O(CH₂)-5-pyrrolidin-2- Cl one 8-128 Cl SMe Cl ¹H NMR, DMSO-d₆, 400 MHz 12.62 (bs, 1H), 7.77 (d, 1H), 7.67 (d, 1H), 2.42 (s, 3H), 8-129 Cl S(O)Me SO₂Me 8-130 Cl CH₂O-tetrahydrofuran- SO₂Et 3-yl 8-131 Cl O(CH₂)₂OMe Cl 8-132 Cl O(CH₂)₂OMe SO₂Me 8-133 Cl O(CH₂)₄OMe SO₂Me 8-134 Cl O(CH₂)₄OMe SO₂Et 8-135 Cl O(CH₂)₃OMe SO₂Me 8-136 Cl O(CH₂)₃OMe SO₂Et 8-137 Cl O(CH₂)₂OMe SO₂Me 8-138 Cl O(CH₂)₂OMe SO₂Et 8-139 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 8-140 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 8-141 Cl SO₂Me Me 8-142 Cl SEt Me 8-143 Cl SOEt Me 8-144 Cl SO₂Et Me 2-145 Cl 4,5-dihydro-1,8-oxazol- SO₂Me 3-yl 8-146 Cl Cl SO₂Me 8-147 F SMe CF₃ 8-148 F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 11.10 (bs, 1H), 8.22 (dd, 1H), 7.71 (dd, 1H), 3.21 (s, 3H) 8-149 OMe SMe CF₃ 8-150 OMe S(O)Me CF₃ 8-151 OMe SO₂Me CF₃ 8-152 Et NH(CH₂)₂OMe SO₂Me 8-153 Et F SO₂Me ¹H NMR, DMSO-d₆, 600 MHz 12.72 (s, 1H), 7.89 (t, 1H), 7.68 (d, 1H), 3.41 (s, 3H), 2.84 (q, 2H), 1.21 (t, 3H) 8-154 Et SMe CF₃ 8-155 CF₃ F SO₂Me 8-156 CF₃ F SO₂Et 8-157 CF₃ O(CH₂)₂OMe SO₂Et 8-158 CF₃ O(CH₂)₃OMe SO₂Et 8-159 CF₃ O(CH₂)₂OMe SO₂Me 8-160 CF₃ O(CH₂)₃OMe SO₂Me 8-161 CF₃ OCH₂CONMe₂ SO₂Me 8-162 CF₃ OCH₂CONMe₂ SO₂Et 8-163 CF₃ OCH₂CONMe₂ Cl 8-164 CF₃ OCH₂CONMe₂ Br 8-165 CF₃ OCH₂CONMe₂ I 8-166 CF₃ OCH₂CONMe₂ F 8-167 CF₃ O(CH₂)₂OMe Cl 8-168 CF₃ O(CH₂)₃OMe Cl 8-169 CF₃ O(CH₂)₂OMe Br 8-170 CF₃ O(CH₂)₃OMe Br 8-171 CF₃ O(CH₂)₂OMe I 8-172 CF₃ O(CH₂)₃OMe I 8-173 CF₃ O(CH₂)₂OMe F 8-174 CF₃ O(CH₂)₃OMe F 8-175 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 8-176 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 8-177 CF₃ [1,4]dioxan-2-yl- Cl methoxy 2-178 CF₃ [1,4]dioxan-2-yl- Br methoxy 8-179 CF₃ [1,4]dioxan-2-yl- I methoxy 8-180 CF₃ [1,4]dioxan-2-yl- F methoxy 8-181 Br OMe Br 8-182 Br O(CH₂)₂OMe Br 8-183 Br O(CH₂)₄OMe SO₂Me 8-184 Br O(CH₂)₄OMe SO₂Et 8-185 Br O(CH₂)₃OMe SO₂Me 8-186 Br O(CH₂)₃OMe SO₂Et 8-187 Br O(CH₂)₂OMe SO₂Me 8-188 Br O(CH₂)₂OMe SO₂Et 8-189 Br [1,4]dioxan-2-yl- SO₂Me methoxy 8-190 Br [1,4]dioxan-2-yl- SO₂Et methoxy 8-191 Br SMe Me 8-192 Br SOMe Me 8-193 Br SO₂Me Me 8-194 Br SEt Me 8-195 Br SOEt Me 8-196 Br SO₂Et Me 8-197 I O(CH₂)₄OMe SO₂Me 8-198 I O(CH₂)₄OMe SO₂Et 8-199 I O(CH₂)₃OMe SO₂Me 8-200 I O(CH₂)₃OMe SO₂Et 8-201 I O(CH₂)₂OMe SO₂Me 8-202 I O(CH₂)₂OMe SO₂Et 8-203 I [1,4]dioxan-2-yl- SO₂Me methoxy 8-204 I [1,4]dioxan-2-yl- SO₂Et methoxy 8-205 I SMe Me 8-206 I SOMe Me 8-207 I SO₂Me Me 8-208 I SEt Me 8-209 I SOEt Me 8-210 I SO₂Et Me 8-211 CH₂SMe OMe SO₂Me 8-212 CH₂OMe OMe SO₂Me 8-213 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 8-214 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 8-215 CH₂O(CH₂)₃OMe OMe SO₂Me 8-216 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 8-217 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 8-218 SO₂Me NH₂ CF₃ 8-219 SO₂Me F CF₃ 8-220 SO₂Me NHEt Cl 8-221 SMe SEt F ¹H NMR, CDCl₃, 400 MHz 12.41 (bs, 1H), 7.58 (dd, 1H), 7.46 (dd, 1H), 3.02 (q, 2H), 2.41 (s, 3H), 1.17 (t, 3H) 8-222 SMe SMe F ¹H NMR, DMSO-d₆, 400 MHz 12.40 (s, 1H), 7.53 (dd, 1H), 7.45 (bd, 1 H), 8-223 Me NH₂ Cl 8-224 Me NH₂ Br 8-225 Me NHMe Cl 8-226 Me NHMe Br 8-227 Me NMe₂ Cl 8-228 Me NMe₂ Br 8-227 Me NMe₂ Cl 8-228 Me NMe₂ Br 8-229 NO₂ O(CH₂)₂OMe Me 8-230 CF₃ S(O)₂Et SO₂Me 8-231 CF₃ S(O)₂Et SO₂Et 8-232 CF₃ SCH₂CONMe₂ SO₂Me 8-233 CF₃ SCH₂CONMe₂ SO₂Et 8-234 CF₃ SCH₂COOH SO₂Me 8-235 CF₃ SCH₂COOH SO₂Et 8-236 Me SO₂—CH₂—CH₂—CH═CH₂ CF₃ 8-237 Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 12.70 (s, 1H), 8.05 (d, 1H), 7.78 (d, 1H), 3.43 (q, 2H), 2.75 (s, 3H), 1.12 (t, 3H) 8-238 CF₃ SEt SO₂Me 8-239 OMe NO₂ Cl 8-240 OMe NH(CO)i-Pr Cl 8-241 OMe NH(CO)CH₂Ph Cl 8-242 CF₃ SEt SO₂Et 8-243 CF₃ S(O)Et SO₂Me 8-244 Cl Me Cl 8-245 Me 3,5-dimethylpyrazol-1-yl SO₂Me 8-246 SMe H CF₃ 8-247 Me 1,2,3-triazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.77 (s, 1H), 8.56 (s, 1H), 8.21 (d, 1H), 8.11 (d, 1H), 8.06 (s, 1H), 3.15 (s, 3H), 1.94 (s, 3H) 8-248 Me Me SMe ¹H NMR, DMSO-d₆, 400 MHz 12.30 (s, 1H), 7.43 (d, 1H), 7.19 (d, 1H), 2.32 (s, 3H), 2.22 (s, 3H) 8-249 Me pyrrolidin-2-on-1-yl SO₂Me 8-250 CF₃ S(O)Et SO₂Et 8-251 Cl pyrazol-1-yl SO₂Me 8-252 Me 3-methylpyrazol-1-yl SO₂Me 8-253 Cl CH₂—N(Et)OMe SO₂Me 8-254 Me Me Cl 8-255 OH Cl Cl 8-256 Me 1,2,4-triazol-1-yl SO₂Me 8-257 Me 4-methoxypyrazol-1-yl SO₂Me 8-258 Me 1,2,4-triazol-1-yl CF₃ 8-259 Me tetrahydropyrimidin- SO₂Me 2(1H)-one-1-yl 8-260 Me NH—(CH₂)₂—O(CO)Et SO₂Me 8-261 Me NH-iPr SO₂Me 8-262 Cl NH—CH₂—(CO)NHEt Cl 8-263 Me NH—CH₂—(CO)NMe₂ SO₂Me 8-264 Me NH—CH₂-furan-2-yl SO₂Me 8-265 Me NH—CH₂—(CO)NHEt SO₂Me 8-266 Me F SO₂Me 8-267 F SO₂Me SO₂Me 8-268 Cl (4-cyclopropyl-3- Cl methyl-5-oxo-4,5- dihydro-1H-1,2,4- triazol-1-yl)methyl 8-269 Cl [4-methyl-5-oxo-3- Cl (2,2,2-trifluorethoxy)- 4,5-dihydro-1H-1,2,4- triazol-1-yl]methyl 8-270 Cl (3-isopropoxy-4-methyl- Cl 5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1-y1]- methyl 8-271 Cl (4-methyl-5-oxo-4,5- Cl dihydro-1H-1,2,4- triazol-1-yl)methyl 8-272 Me Cl SO₂Et 8-273 SO₂Me F Cl 8-274 Me 1,2,3-triazol-1-yl SO₂Me 8-275 Me isobutyl(methyl)- SO₂Me carbamoylamino 8-276 Me 3-oxomorpholin-4-yl SO₂Me 8-277 OMe [ethyl(methylsulfonyl)- Cl amino]methyl 8-278 F SO₂Me CF₃ 8-279 OMe benzoylamino Cl 8-280 OMe cyclopropylcarbonyl- Cl amino 8-281 OMe propionylamino Cl 8-282 NO₂ SO₂Me SO₂Me 8-283 NO₂ SO₂Me Cl 8-284 NO₂ SOMe SO₂Me 8-285 NO₂ SOMe Br 8-286 NO₂ SOMe Cl 8-287 NO₂ SMe SO₂Me 8-288 NO₂ SMe Br 8-289 NO₂ SMe Cl 8-290 Cl CH₂OCH(CH₃)₂ SO₂Et 8-291 Cl CH₂OEt SO₂Et 8-292 Cl CH₂OMe SO₂Et 8-293 Cl CH₂OCH₂C₂F₅ SO₂Me 8-294 Cl CH₂OCH₂CHF₂ SO₂Me 8-295 Cl CH₂OCH₂CCH SO₂Et 8-296 Cl CH₂OC₂H₄OMe SO₂Me 8-297 Cl CH₂(OC₂H₄)₂OMe SO₂Me 8-298 Cl 5-ethoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 8-299 Cl 5-methoxymethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 8-300 Et SOMe CF₃ 8-301 iPr SMe CF₃ 8-302 Et SMe CF₃ 8-303 Et SO₂Me CF₃ 8-304 cPr SOMe CF₃ 8-305 CH═CH₂ SMe CF₃ 8-306 Et SMe Cl 8-307 Et SO₂Me Cl 8-308 Cl NMe₂ Cl 8-309 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 8-313 Me SO₂(CH₂)₂OMe CF₃ 8-314 Me SOEt SO₂Me 8-315 Me SO₂Et SO₂Me 8-316 Me SMe 1,2,4- triazol-1-yl 8-317 OEt SMe CF₃ 8-318 Me S(CH₂)₂OMe CF₃ 8-319 Me SOMe 1,2,4- triazol-1-yl 8-320 OEt SOMe CF₃ 8-321 Me SO(CH₂)₂OMe CF₃ 8-322 Me SCH₂CCMe SO₂Me 8-323 Me S—c-Pen SO₂Me 8-324 OMe SMe OMe 8-325 Me SCH₂CH═CHCH₃ SO₂Me 8-326 Me SOCH₂CCMe SO₂Me 8-327 Me SO₈—c-Pen SO₂Me 8-328 Me SO—c-Pen SO₂Me 8-329 Me S(CH₂)₃Cl SO₂Me 8-330 Me SCH₂(4-F—Ph) SO₂Me 8-331 Me SO₂CH₂CCMe SO₂Me 8-332 Me SO₂CH₂CH═CHCH₃ SO₂Me 8-333 Me SOCH₂CH═CHCH₃ SO₂Me 8-334 Me SOCH₂-epoxy-Me SO₂Me 8-335 Me SO₂(CH₂)₃Cl SO₂Me 8-336 Me SO(CH₂)₃Cl SO₂Me 8-337 Me SOCH₂(4-F—Ph) SO₂Me 8-338 Me SO₂CH₂(4-F—Ph) SO₂Me 8-339 Me SO₂Me C₂F₅ 8-340 O(CH₂)₂OMe SMe CF₃ 8-341 O(CH₂)₂OMe SO₂Me CF₃ 8-342 O(CH₂)₂OMe SOMe CF₃ 8-343 Me S(CH₂)₂OCH₂CF₃ SO₂Me 8-344 Me SO(CH₂)₂OCH₂CF₃ SO₂Me 8-345 Me SO₂(CH₂)₂OCH₂CF₃ SO₂Me 8-346 OEt SEt CF₃ 8-347 O—CH₂—c-Pr SMe CF₃ 8-348 OMe SEt CF₃ 8-349 OMe SO₂Et CF₃ 8-350 OMe SOEt CF₃ 8-351 OEt SO₂Et CF₃ 8-352 OEt SOEt CF₃ 8-353 O—CH₂—c-Pr SOMe CF₃ 8-354 O—CH₂—c-Pr SO₂Me CF₃ 8-355 Me SEt SO₂Me

TABLE 9 Compounds of the general formula (I) according to the invention in which R is a radical OR*

No. R* X Y Z Physical data 9-50 Me NO₂ O(CH₂)₂OMe OMe 9-51 Me NO₂ OMe Me 9-52 Me NO₂ NH₂ OMe 9-53 Me NO₂ NH₂ SO₂Me 9-54 Me NO₂ NH₂ Cl 9-55 Me NO₂ NHMe Cl 9-56 Me NO₂ NMe₂ Cl 9-57 Me NO₂ NH₂ Br 9-58 Me NO₂ NHMe Br 9-59 Me NO₂ NMe₂ Br 9-60 Me NO₂ NH₂ F 9-61 Me NO₂ NHMe F 9-62 Me NO₂ NMe₂ F 9-63 Me NO₂ NH₂ SO₂Me 9-64 Me NO₂ NHMe SO₂Me 9-65 Me NO₂ NMe₂ SO₂Me 9-66 Me NO₂ NH₂ 1H-1,2,4- triazol-1-yl 9-67 Me NO₂ NHMe 1H-1,2,4- triazol-1-yl 9-68 Me NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 9-69 Me Me F F ¹H NMR, DMSO-d₆, 400 MHz 11.22 (s, 1H), 7.45-7.40 (m, 2H), 4.09 (s, 3H), 2.34 (d, 3H) 9-70 Me Me F Cl 9-71 Me Me SMe CF₃ 9-72 Me Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.49 (s, 1H), 8.03 (d, 1H), 7.71 (d, 1H), 4.10 (s, 3H), 3.43 (s, 3H), 2.46 (s, 3H) 9-73 Me Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.51 (s, 1H), 8.24 (d, 1H), 7.99 (d, 1H), 4.11 (s, 3H), 3.60 (s, 3H), 3.57 (s, 3H), 2.67 (s, 3H) 9-74 Et Me SO₂Me SO₂Me 9-75 n-Pr Me SO₂Me SO₂Me 9-76 i-Pr Me SO₂Me SO₂Me 9-77 t-Bu Me SO₂Me SO₂Me 9-78 Ph Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.80 (s, 1H), 8.25 (d, 1H), 7.96 (d, 1H), 7.49 (m, 2H), 7.39 (d, 2H), 7.30 (t, 1H), 3.59 (s, 3H), 3.56 (s, 3H), 2.69 (s, 3H) 9-79 Me Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 8.02 (d, 1H), 7.92 (d, 1H), 4.11 (s, 3H), 3.31 (s, 3H), 2.70 (s, 3H) 9-80 Et Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.47 (s, 1H), 8.01 (d, 1H), 7.94 (d, 1H), 4.43 (q, 2H), 3.42 (s, 3H), 2.72(s, 3H), 1.40 (t, 3H) 9-81 n-Pr Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.46 (s, 1H), 8.02 (d, 1H), 7.95 (d, 1H), 4.34 (t, 2H), 3.42 (s, 3H), 2.73 (s, 3H), 1.80 (m, 2H), 0.98 (t, 3H) 9-82 i-Pr Me SO₂Me CF₃ 9-83 t-Bu Me SO₂Me CF₃ 9-84 Ph Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.78 (s, 1H), 8.02 (d, 1H), 7.91 (d, 1H), 7.50 (m, 2H), 7.40 (d, 2H), 7.31 (t, 1H), 3.42 (s, 3H), 2.72 (s, 3H) 9-85 Me Me Cl CF₃ 9-86 Me Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.48 (s, 1H), 7.85 (d, 1H), 7.80 (d, 1H), 4.10 (s, 3H), 3.04 (s, 3H), 2.83 (s, 3H) 9-87 Me Me SEt OMe 9-88 Me Me NMe₂ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.33 (s, 1H), 7.84 (d, 1H), 7.52 (d, 1H), 4.09 (s, 3H), 3.33 (s, 3H), 2.83 (s, 6H), 2.36 (s, 3H) 9-89 Et Me NMe₂ SO₂Me 9-90 n-Pr Me NMe₂ SO₂Me 9-91 i-Pr Me NMe₂ SO₂Me 9-92 t-Bu Me NMe₂ SO₂Me 9-93 Ph Me NMe₂ SO₂Me 9-94 Me Me NH(CH₂)₂OMe SO₂Me 9-95 Et Me NH(CH₂)₂OMe SO₂Me 9-96 n-Pr Me NH(CH₂)₂OMe SO₂Me 9-97 i-Pr Me NH(CH₂)₂OMe SO₂Me 9-98 t-Bu Me NH(CH₂)₂OMe SO₂Me 9-99 Ph Me NH(CH₂)₂OMe SO₂Me 9-100 Me Me O(CH₂)₄OMe SO₂Me 9-101 Me Me NH₂ SO₂Me 9-102 Me Me O(CH₂)₂—O(3,5- SO₂Me dimethoxy- pyrimidin-2-yl 9-103 Me Me O(CH₂)₂—O—NMe₂ Cl 9-104 Me Me O(CH₂)₂—NH(CO)NMe₂ Cl 9-105 Me Me O(CH₂)-5- Br pyrrolidin-2-one 9-106 Me Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 9-107 Me Me O(CH₂)—(CO)NEt₂ Br 9-108 Me Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H- 1,2,4-triazol-3- one 9-109 Me Me O(CH₂)-3,5- Cl dimethyl-1,2- oxazol-4-yl 9-110 Me Me O(CH₂)₂—NHCO₂Me Cl 9-111 Me Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 9-112 Et Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 9-113 n-Pr Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 9-114 i-Pr Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 9-115 t-Bu Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 9-116 Ph Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 9-117 Me Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.34 (s, 1H), 7.98 (d, 1H), 7.51 (d, 1H), 4.10 (s, 3H), 3.24 (s, 3H), 2.61 (s, 3H), 2.31 (s, 3H) 9-118 Me Me OH SO₂Me 9-119 Me Me O—CH₂—NHSO₂cPr Cl 9-120 Me Me O—CH₂—NHSO₂Me SO₂Me 9-121 Et Me O—CH₂—NHSO₂Me SO₂Me 9-122 n-Pr Me O—CH₂—NHSO₂Me SO₂Me 9-123 i-Pr Me O—CH₂—NHSO₂Me SO₂Me 9-124 t-Bu Me O—CH₂—NHSO₂Me SO₂Me 9-125 Ph Me O—CH₂—NHSO₂Me SO₂Me 9-126 Me Me SMe Cl 9-127 Me Me SOMe Cl 9-128 Et Me SO₂Me Cl 9-129 n-Pr Me SO₂Me Cl 9-130 i-Pr Me SO₂Me Cl 9-131 t-Bu Me SO₂Me Cl 9-132 Ph Me SO₂Me Cl 9-133 Me Me SO₂Me Cl 9-134 Me Me SMe Br 9-135 Me Me SOMe Br 9-136 Me Me SO₂Me Br 9-137 Me Me SMe I 9-138 Me Me SOMe I 9-139 Me Me SO₂Me I 9-140 Me Me SEt Cl 9-141 Me Me SOEt Cl 9-142 Me Me SO₂Et Cl 9-143 Me Me SEt Br 9-144 Me Me SOEt Br 9-145 Me Me SO₂Et Br 9-146 Me Me SEt I 9-147 Me Me SOEt I 9-148 Me Me SO₂Et I 9-149 Me Me SEt F 9-150 Me Me SOEt F 9-151 Me Me SO₂Et F 9-152 Me Me S(O)Me SO₂Me 9-153 Me Me SMe SO₂Me 9-154 Me Me SMe OMe 9-155 Me Me S(O)Me OMe 9-156 Me Me SO₂Me OMe 9-157 Me Me SMe Cl 9-158 Me Me S(O)Me Cl 9-159 Me Me SO₂Me Cl 9-160 Me Me [1,4]dioxan-2-yl- SO₂Me methoxy 9-161 Me Me [1,4]dioxan-2-yl- SO₂Et methoxy 9-162 Me Me O(CH₂)₄OMe SO₂Et 9-163 Me Me O(CH₂)₃OMe SO₂Me 9-164 Me Me O(CH₂)₃OMe SO₂Et 9-165 Me Me O(CH₂)₂OMe SO₂Me 9-166 Me Me O(CH₂)₂OMe SO₂Et 9-167 Me Me S(O)Me SO₂Me 9-168 Me Me SMe SO₂Me 9-169 Me Me SMe OMe 9-170 Me Me S(O)Me OMe 9-171 Me Me SO₂Me OMe 9-172 Me Cl OCH₂(CO)NMe₂ Cl 9-173 Me Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.72 (s, 1H), 8.12 (d, 1H), 7.87 (d, 1H), 4.10 (s, 3H), 3.48 (s, 3H), 2.46 (s, 3H) 9-174 Me Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.15 (d, 1H), 8.0 (bs, 1H), 7.81 (d, 1H), 5.35 (s, 2H), 4.18 (s, 3H), 4.05 (q, 2H), 3.21 (s, 3H) 9-175 Et Cl CH₂OCH₂CF₃ SO₂Me 9-176 n-Pr Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.57 (s, 1H), 8.11 (d, 1H), 7.98 (d, 1H), 5.25 (s, 2H), 4.33 (q, 2H), 4.31 (q, 2H), 3.37 (s, 3H), 1.78 (m, 2H), 0.98 (t, 3H) 9-177 i-Pr Cl CH₂OCH₂CF₃ SO₂Me 9-178 t-Bu Cl CH₂OCH₂CF₃ SO₂Me 9-179 Ph Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.91 (s, 1H), 8.11 (d, 1H), 7.86 (d, 1H), 7.50 (m, 2H), 7.40 (d, 2H), 7.31 (t, 1H), 5.25 (s, 2H), 4.29 (q, 2H), 3.36 (s, 3H) 9-180 Me Cl 5-cyanomethyl- SO₂Et ¹H NMR, CDCl₃, 400 MHz 4,5-dihydro-1,2- 8.15 (bs, 1H), 8.10 (d, 1H), 7.95 oxazol-3-yl (bs, 1H), 5.17 (m, 1H), 4.18 (s, 3H), 3.72 (m, 1H), 3.37 (q, 2H), 3.25 (m, 1H), 2.80-2.98 (m, 2H), 1.30 (t, 3H) 9-181 Et Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 9-182 n-Pr Cl 5-cyanomethyl- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 4,5-dihydro-1,2- 11.60 (s, 1H), 8.11 (d, 1H), 8.05 oxazol-3-yl (d, 1H), 5.19 (m, 1H), 4.32 (m, 2H), 3.59 (m, 1H), 3.42 (q, 2H), 3.15 (dd, 1H), 3.01 (m, 2H), 1.77 (m, 2H), 1.15 (t, 3H), 0.95 (t, 3H) 9-183 i-Pr Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 9-184 t-Bu Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 9-185 Ph Cl 5-cyanomethyl- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 4,5-dihydro-1,2- 11.93 (s, 1H), 8.11 (d, 1H), 8.00 oxazol-3-yl (d, 1H), 7.50 (m, 2H), 7.41 (d, 2H9, 7.32 (t, 1H), 5.19 (m, 1H), 3.50 (dd, 2H), 3.44 (q, 2H), 3.31 (s, 1H), 3.15 (dd, 2H), 3.02 (m, 2H), 1.16 (t, 3H) 9-186 Me Cl CH₂O- SO₂Me tetrahydro- furan-3-yl 9-187 Et Cl CH₂O- SO₂Me tetrahydro- furan-3-yl 9-188 n-Pr Cl CH₂O- SO₂Me tetrahydro- furan-3-yl 9-189 i-Pr Cl CH₂O- SO₂Me tetrahydro- furan-3-yl 9-190 t-Bu Cl CH₂O- SO₂Me tetrahydro- furan-3-yl 9-191 Ph Cl CH₂O- SO₂Me tetrahydro- furan-2-yl 9-192 Me Cl SMe SO₂Me 9-193 Me Cl F SMe 9-194 n-Pr Cl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydrofuran- 11.58 (bs, 1H), 8.09 (d, 1H), 7.85 2-yl (d, 1H), 5.08 (m, 2H), 4.32 (t, 2H), 3.97 (m, 1H), 3.71 (dd, 1H), 3.65- 3.51 (m, 3H), 3.38 (s, 3H), 1.90- 1.70 (m, 5H), 1.53 (m, 1H), 0.95 (t, 3H) 9-195 Me Cl CH₂OCH₂- SO₂Et tetrahydrofuran- 3-yl 9-196 n-Pr Cl O(CH₂)-5- Cl pyrrolidin-2-one 9-197 Me Cl O(CH₂)-5- Cl pyrrolidin-2-one 9-198 Me Cl O(CH₂)-5- Cl pyrrolidin-2-one 9-199 Me Cl S(O)Me SO₂Me 9-200 Me Cl CH₂O- SO₂Et ¹H NMR, CDCl₃, 400 MHz tetrahydro- 8.37 (bs, 1H), 8.0 (d, 1H), 7.73 (d, furan-3-yl 1H), 5.07 (m, 2H), 4.34 (m, 1H), 4.18 (s, 3H), 3.73-3.94 (m, 4H), 3.36 (q, 2H), 2.08 (m, 2H), 1.25 (t, 3H) 9-201 Me Cl SMe Cl ¹H NMR, CDCl₃, 400 MHz 8.03 (s, 1H), 7.66 (d, 1H), 4.19 (s, 3H), 2.47 (s, 3H) 9-202 Me Cl O(CH₂)₂OMe Cl 9-203 Et Cl O(CH₂)₂OMe Cl 9-204 n-Pr Cl O(CH₂)₂OMe Cl 9-205 i-Pr Cl O(CH₂)₂OMe Cl 9-206 t-Bu Cl O(CH₂)₂OMe Cl 9-207 Ph Cl O(CH₂)₂OMe Cl 9-208 Me Cl O(CH₂)₄OMe SO₂Me 9-209 Me Cl O(CH₂)₄OMe SO₂Et 9-210 Me Cl O(CH₂)₃OMe SO₂Me 9-211 Me Cl O(CH₂)₃OMe SO₂Et 9-212 Me Cl O(CH₂)₂OMe SO₂Me 9-213 Me Cl O(CH₂)₂OMe SO₂Et 9-214 Me Cl [1,4]dioxan-2-yl- SO₂Me methoxy 9-215 Me Cl [1,4]dioxan-2-yl- SO₂Et methoxy 9-216 Me Cl SO₂Me Me 9-217 Me Cl SEt Me 9-218 Me Cl SOEt Me 9-219 Me Cl SO₂Et Me 9-220 Me Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 9-221 Me Cl Cl SO₂Me 9-222 Me F SMe CF₃ 9-223 n.Pr F SMe CF₃ 9-224 n-Pr F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.73 (bd, 1H), 8.47 (dd, 1H), 7.74 (bd, 1H), 4.41 (t, 2H), 3.14 (s, 3H), 1.79 (m, 2H), 1.03 (t, 3H) 9-225 Me F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.85 (b, 1H), 8.49 (dd, 1H), 7.74 (dd, 1H), 7.69 (bs, 1H), 4.18 (s, 3H), 3.13 (s, 3H) 9-226 F S(O)Me CF₃ 9-227 Me F SO₂Me CF₃ 9-228 n.Pr F SO₂Me CF₃ 9-229 Me SMe SEt F ¹H NMR, CDCl₃, 400 MHz 10.02 (bs, 1H), 8.49 (b, 1H), 8.20 (dd, 1H), 7.96 (b, 1H), 7.22 (dd, 1H), 4.40 (t, 3H), 3.05 (q, 2H), 2.49 (s, 3H), 1.88 (m, 2H), 1.26 (t, 2H), 1.05 (t, 3H) 9-230 n-Pr SMe SEt F ¹H NMR, CDCl₃, 400 MHz 9.75 (bs, 1H), 8.49 (b, 1H), 8.20 (dd, 1H), 7.94 (b, 1H), 7.18 (dd, 1H), 4.19 (s, 3H), 3.00 (s, 3H), 2.49 (s, 3H), 1.28 (t, 3H) 9-231 Me OMe SMe CF₃ 9-232 Me OMe S(O)Me CF₃ 9-233 Me OMe SO₂Me CF₃ 9-234 Me Et NH(CH₂)₂OMe SO₂Me 9-235 Me Et F SO₂Me 9-236 Me Et SMe CF₃ 9-237 Me CF₃ F SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.76 (s, 1H), 8.27 (t, 1H), 7.79 (d, 1H), 4.11 (s, 3H), 3.48 (s, 3H) 9-238 Me CF₃ F SO₂Et 9-239 Me CF₃ O(CH₂)₂OMe SO₂Et 9-240 Me CF₃ O(CH₂)₃OMe SO₂Et 9-241 Me CF₃ O(CH₂)₂OMe SO₂Me 9-242 Me CF₃ O(CH₂)₃OMe SO₂Me 9-243 Me CF₃ OCH₂CONMe₂ SO₂Me 9-244 Me CF₃ OCH₂CONMe₂ SO₂Et 9-245 Me CF₃ OCH₂CONMe₂ Cl 9-246 Me CF₃ OCH₂CONMe₂ Br 9-247 Me CF₃ OCH₂CONMe₂ I 9-248 Me CF₃ OCH₂CONMe₂ F 9-249 Me CF₃ O(CH₂)₂OMe Cl 9-250 Me CF₃ O(CH₂)₃OMe Cl 9-251 Me CF₃ O(CH₂)₂OMe Br 9-252 Me CF₃ O(CH₂)₃OMe Br 9-253 Me CF₃ O(CH₂)₂OMe I 9-254 Me CF₃ O(CH₂)₃OMe I 9-255 Me CF₃ O(CH₂)₂OMe F 9-256 Me CF₃ O(CH₂)₃OMe F 9-257 Me CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 9-258 Me CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 9-259 Me CF₃ [1,4]dioxan-2-yl- Cl methoxy 9-260 Me CF₃ [1,4]dioxan-2-yl- Br methoxy 9-261 Me CF₃ [1,4]dioxan-2-yl- I methoxy 9-262 Me CF₃ [1,4]dioxan-2-yl- F methoxy 9-263 Me Br OMe Br 9-264 Me Br O(CH₂)₂OMe Br 9-265 Me Br O(CH₂)₄OMe SO₂Me 9-266 Me Br O(CH₂)₄OMe SO₂Et 9-267 Me Br O(CH₂)₃OMe SO₂Me 9-268 Me Br O(CH₂)₃OMe SO₂Et 9-269 Me Br O(CH₂)₂OMe SO₂Me 9-270 Me Br O(CH₂)₂OMe SO₂Et 9-271 Me Br [1,4]dioxan-2-yl- SO₂Me methoxy 9-272 Me Br [1,4]dioxan-2-yl- SO₂Et methoxy 9-273 Me Br SMe Me 9-274 Me Br SOMe Me 9-275 Me Br SO₂Me Me 9-276 Me Br SEt Me 9-277 Me Br SOEt Me 9-278 Me Br SO₂Et Me 9-279 Me I O(CH₂)₄OMe SO₂Me 9-280 Me I O(CH₂)₄OMe SO₂Et 9-281 Me I O(CH₂)₃OMe SO₂Me 9-282 Me I O(CH₂)₃OMe SO₂Et 9-283 Me I O(CH₂)₂OMe SO₂Me 9-284 Me I O(CH₂)₂OMe SO₂Et 9-285 Me I [1,4]dioxan-2-yl- SO₂Me methoxy 9-286 Me I [1,4]dioxan-2-yl- SO₂Et methoxy 9-287 Me I SMe Me 9-288 Me I SOMe Me 9-289 Me I SO₂Me Me 9-290 Me I SEt Me 9-291 Me I SOEt Me 9-292 Me I SO₂Et Me 9-293 Me CH₂SMe OMe SO₂Me 9-294 Me CH₂OMe OMe SO₂Me 9-295 Me CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 9-296 Me CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 9-297 Me CH₂O(CH₂)₃OMe OMe SO₂Me 9-298 Me CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 9-299 Me CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 9-300 Me SO₂Me NH₂ CF₃ 9-301 Me SO₂Me F CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.57 (s, 1H), 8.28 (t, 1H), 7.70 (d, 1H), 4.10 (s, 3H), 3.45 (s, 3H) 9-302 Me SO₂Me NHEt Cl 9-303 Me SMe SEt F 9-304 Me SMe SMe F ¹H NMR, CDCl₃, 400 MHz 9.85 (bs, 1H), 7.91 (bs, 1H), 7.20 (dd, 1H), 4.19 (s, 3H), 2.56 (s, 3H), 2.49 (s, 3H) 9-305 n-Pr SMe SMe F ¹H NMR, CDCl₃, 400 MHz 10.00 (bs, 1H), 7.96 (b, 1H), 7.20 (dd, 1H), 4.39 (t, 2H), 2.56 (s, 3H), 2.49 (s, 3H), 1.88 (m, 2H), 1.04 (t, 3H). 9-306 Benzyl Me SO₂Me CF₃ 9-307 Me Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.60 (s, 1H), 7.97 (d, 1H), 7.69 (d, 1H), 4.10 (s, 3H), 3.41 (q, 2H), 2.72 (s, 3H), 1.12 (t, 3H) 9-308 Benzyl Me SO₂Me CF₃ 9-309 Benzyl Me SO₂Me SO₂Me 9-310 Benzyl Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 7.84 (d, 1H), 7.80 (d, 1H), 7.52 (d, 2H), 7.40 (m, 3H), 7.30 (t, 1H), 5.45 (s, 2H), 3.03 (s, 3H), 2.80 (s, 3H) 9-311 Me Cl 1H-pyrazo1-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.76 (s, 1H), 8.19 (d, 1H), 8.06 (d, 1H), 8.01 (s, 1H), 7.87 (s, 1H), 4.10 (s, 3H), 3.19 (s, 3H) 9-312 Me Me F SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.28 (s, 1H), 7.57 (t, 1H), 7.41 (d, 1H), 4.09 (s, 3H), 2.33 (d, 3H) 9-313 Me Me 1H-1,2,3-triazol- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.62 (s, 1H), 8.53 (s, 1H), 8.14 (d, 1H), 8.06 (s, 1H), 8.03 (d, 1H), 4.10 (s, 3H), 3.14 (s, 3H), 1.89 (s, 3H) 9-314 Me Cl Me Cl ¹H NMR, DMSO-d₆, 400 MHz 11.39 (s, 1H), 7.57 (d, 1H), 7.45 (d, 1H), 4.09 (s, 3H), 2.47 (s, 3H) 9-315 Me Cl CH₂OCH₂-2- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydrofuran- 11.65 (s, 1H), 8.08 (d, 1H), 7.85 2-yl (d, 1H), 5.08 (s, 2H), 4.10 (s, 3H), 3.97 (m, 1H), 3.70 (q, 1H), 3.65- 3.52 (m, 3H), 3.38 (s, 3H), 1.94- 1.72 (m, 3H), 1.55 (m, 1H) 9-316 Me Me Me SMe ¹H NMR, DMSO-d₆, 400 MHz 10.98 (s, 1H), 7.33 (d, 1H), 7.15 (d, 1H), 4.08 (s, 3H), 2.25 (s, 3H), 2.23 (s, 3H) 9-317 Ph Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.73 (s, 1H), 7.86 (d, 1H), 7.76 (d, 1H), 7.49 (m, 2H), 7.41 (d, 2H), 7.31 (t, 1H), 3.04 (s, 3H), 2.84 (s, 3H) 9-318 Me Cl S(O)Me Cl ¹H NMR, DMSO-d₆, 400 MHz 11.58 (s, 1H), 7.85 (d, 1H), 7.81 (d, 1H), 4.10 (s, 3H), 3.51 (s, 3H) 9-319 Me Cl CH₂N(OMe)Et SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.59 (s, 1H), 8.11 (d, 1H), 7.82 (d, 1H), 4.52 (s, 2H), 4.10 (s, 3H), 3.57 (s, 3H), 3.17 (s, 3H), 2.85 (q, 2H), 1.14 (t, 3H) 9-320 n-Pr Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.49 (s, 1H), 7.99 (d, 1H), 7.70 (d, 1H), 4.33 (t, 2H), 3.42 (q, 2H), 2.73 (s, §H), 1.79 (m, 2H), 1.14 (t, 3H), 0.98 (t, 3H) 9-321 Me Me 4-methoxy-1H- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz pyrazol-1-yl 11.54(s, 1H), 8.05 (d, 1H), 7.91 (d, 1H), 7.73 (s, 1H), 7.66 (s, 1H), 4.09 (s, 3H), 3.75 (s, 3H), 3.10 (s, 3H), 1.92 (s, 3H) 9-322 Ph Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.73 (s, 1H), 8.03 (d, 1H), 7.67 (d, 1H), 7.49 (m, 2H), 7.38 (d, 2H), 7.30 (t, 1H), 3.43 (s, 3H), 2.45 (s, 3H) 9-323 n-Pr Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.42 (s, 1H), 7.86 (d, 1H), 7.81 (d, 1H), 4.34 (t, 2H), 3.05 (s, 3H), 2.85 (s, 3H), 1.79 (m, 2H), 0.98 (t, 3H)

TABLE 10 Compounds of the general formula (I) according to the invention

No. R X Y Z Physical data 10-46 Ph NO₂ O(CH₂)₂OMe OMe 10-47 Ph NO₂ OMe Me 10-48 Ph NO₂ NH₂ OMe 10-49 Ph NO₂ NH₂ SO₂Et 10-50 Ph NO₂ NH₂ Cl 10-51 Ph NO₂ NHMe Cl 10-52 Ph NO₂ NMe₂ Cl 10-53 Ph NO₂ NH₂ Br 10-54 Ph NO₂ NHMe Br 10-55 Ph NO₂ NMe₂ Br 10-56 Ph NO₂ NH₂ F 10-57 Ph NO₂ NHMe F 10-58 Ph NO₂ NMe₂ F 10-59 Ph NO₂ NH₂ SO₂Me 10-60 Ph NO₂ NHMe SO₂Me 10-61 Ph NO₂ NMe₂ SO₂Me 10-62 Ph NO₂ NH₂ 1H-1,2,4- triazol-1-yl 10-63 Ph NO₂ NHMe 1H-1,2,4- triazol-1-yl 10-64 Ph NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 10-65 Ph Me F F 10-66 Ph Me F Cl 10-67 Ph Me SMe CF₃ 10-68 Ph Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.58 (s, 1 H), 8.05 (d, 1H), 7.78 (m, 3H), 7.58 (m, 3H), 7.59 (m, 3H), 3.42 (s, 3H), 2.39 (s, 3H) 10-69 Ph Me SO₂Me SO₂Me 10-70 4-Cl—Ph Me SO₂Me SO₂Me 10-71 1-ethylbenz- Me SO₂Me SO₂Me imidazol-2-yl 10-72 1,2,4-triazol-1-yl Me SO₂Me SO₂Me 10-73 benzoxazol-2-yl Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.90 (s, 1H), 9.39 (s, 1H), 8.47 (s, 1H), 8.28 (d, 1H), 8.06 (d, 1H), 3.59 (s, 3H), 3.56 (s, 3H), 2.69 (s, 3H) 10-74 Ph Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.60 (s, 1H), 8.03 (d, 1H), 7.99 (d, 1H), 7.79 (m, 2H), 7.69 (m, 3H), 3.41 (s, 3H), 2.66 (s, 3H) 10-75 4-Cl—Ph Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.63 (s, 1H), 8.05 (d, 1H), 8.01 (d, 1H), 7.81 (m, 2H), 7.67 (m, 2H), 3.41 (s, 3H), 2.67 (s, 3H) 10-76 1-ethylbenz- Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz imidazol-2-yl 11.85 (s, 1H), 8.18 (d, 1H), 8.14 (d, 1H), 7.84 (d, 1H), 7.80 (d, 1H), 7.46 (t, 1H), 7.37 (t, 1H), 4.68 (q, 2H), 3.45 (s, 3H), 2.82 (s, 3H), 1.43 (t, 3H) 10-77 1,2,4-triazol-1-yl Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.90 (s, 1H), 9.39 (s, 1H), 8.47 (s, 1H), 8.06 (d, 1H), 8.00 (d, 1H), 3.42 (s, 3H), 2.73 (s, 3H) 10-78 benzoxazol-2-yl Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.95 (s, 1H), 8.13 (s, 2H), 7.96 (d, 1H), 7.94 (d, 1H), 7.61 (t, 1H), 7.55 (t, 1H), 3.44 (s, 3H), 2.82 (s, 3H) 10-79 Ph Me Cl CF₃ 10-80 Ph Me S(O)Me CF₃ 10-81 Ph Me SEt OMe 10-82 Ph Me NMe₂ SO₂Me 10-83 4-Cl—Ph Me NMe₂ SO₂Me 10-84 1-ethylbenz- Me NMe₂ SO₂Me imidazol-2-yl 10-85 1,2,4-triazol-1-yl Me NMe₂ SO₂Me 10-86 benzoxazol-2-yl Me NMe₂ SO₂Me 10-87 Ph Me NH(CH₂)₂OMe SO₂Me 10-88 4-Cl—Ph Me NH(CH₂)₂OMe SO₂Me 10-89 1-ethylbenz- Me NH(CH₂)₂OMe SO₂Me imidazol-2-yl 10-90 1,2,4-triazol-1-yl Me NH(CH₂)₂OMe SO₂Me 10-91 benzoxazol-2-yl Me NH(CH₂)₂OMe SO₂Me 10-92 Ph Me O(CH₂)₄OMe SO₂Me 10-93 Ph Me NH₂ SO₂Me 10-94 Ph Me O(CH₂)₂—O(3,5-di- SO₂Me methoxy- pyrimidin-2-yl 10-95 Ph Me O(CH₂)₂—O—NMe₂ Cl 10-96 Ph Me O(CH₂)₂—NH(CO)NMe₂ Cl 10-97 Ph Me O(CH₂)-5- Br pyrrolidin-2-one 10-98 Ph Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 10-99 Ph Me O(CH₂)—(CO)NEt₂ Br 10-100 Ph Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H- 1,2,4-triazol-3-one 10-101 Ph Me O(CH₂)-3,5- Cl dimethyl-1,2- oxazol-4-yl 10-102 Ph Me O(CH₂)₂—NHCO₂Me Cl 10-103 Ph Me 4,5-dihydro- SO₂Me 1,2-oxazol-3-yl 10-104 4-Cl—Ph Me 4,5-dihydro- SO₂Me 1,2-oxazol-3-yl 10-105 1-ethylbenz- Me 4,5-dihydro- SO₂Me imidazol-2-yl 1,2-oxazol-3-yl 10-106 1,2,4-triazol-1-yl Me 4,5-dihydro- SO₂Me 1,2-oxazol-3-yl 10-107 benzoxazol-2-yl Me 4,5-dihydro- SO₂Me 1,2-oxazol-3-yl 10-108 Ph Me Me SO₂Me 10-109 Ph Me OH SO₂Me 10-110 Ph Me O—CH₂—NHSO₂cPr Cl 10-111 Ph Me O—CH₂—NHSO₂Me SO₂Me 10-112 4-Cl—Ph Me O—CH₂—NHSO₂Me SO₂Me 10-113 1-ethylbenz- Me O—CH₂—NHSO₂Me SO₂Me imidazol-2-yl 10-114 1,2,4-triazol-1-yl Me O—CH₂—NHSO₂Me SO₂Me 10-115 benzoxazol-2-yl Me O—CH₂—NHSO₂Me SO₂Me 10-116 Ph Me SMe Cl 10-117 Ph Me SOMe Cl 10-118 4-Cl—Ph Me SO₂Me Cl 10-119 1-ethylbenz- Me SO₂Me Cl imidazol-2-yl 10-120 1,2,4-triazol-1-yl Me SO₂Me Cl 10-121 benzoxazol-2-yl Me SO₂Me Cl 10-122 Ph Me S(O)Me SO₂Me 10-123 Ph Me SMe SO₂Me 10-124 Ph Me SMe OMe 10-125 Ph Me S(O)Me OMe 10-126 Ph Me SO₂Me OMe 10-127 Ph Me SMe Cl 10-128 Ph Me S(O)Me Cl 10-129 Ph Me SO₂Me Cl 10-130 Ph Me [1,4]dioxan-2- SO₂Me ylmethoxy 10-131 Ph Me [1,4]dioxan-2- SO₂Et ylmethoxy 10-132 Ph Me O(CH₂)₄OMe SO₂Et 10-133 Ph Me O(CH₂)₃OMe SO₂Me 10-134 Ph Me O(CH₂)₃OMe SO₂Et 10-135 Ph Me O(CH₂)₂OMe SO₂Me 10-136 Ph Me O(CH₂)₂OMe SO₂Et 10-137 Ph Me S(O)Me SO₂Me 10-138 Ph Me SMe SO₂Me 10-139 Ph Me SMe OMe 10-140 Ph Me S(O)Me OMe 10-141 Ph Me SO₂Me OMe 10-142 Ph Me SMe Cl 10-143 Ph Me S(O)Me Cl 10-144 Ph Me SO₂Me Cl 10-145 Ph Me SMe Br 10-146 Ph Me SOMe Br 10-147 Ph Me SO₂Me Br 10-148 Ph Me SMe I 10-149 Ph Me SOMe I 10-150 Ph Me SO₂Me I 10-151 Ph Me SEt Cl 10-152 Ph Me SOEt Cl 10-153 Ph Me SO₂Et Cl 10-154 Ph Me SEt Br 10-155 Ph Me SOEt Br 10-156 Ph Me SO₂Et Br 10-157 Ph Me SEt I 10-158 Ph Me SOEt I 10-159 Ph Me SO₂Et I 10-160 Ph Me SEt F 10-161 Ph Me SOEt F 10-162 Ph Me SO₂Et F 10-163 Ph Cl OCH₂(CO)NM Cl 10-164 Ph Cl Cl SO₂Me 10-165 Ph Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.72 (s, 1H), 8.12 (d, 1H), 7.94 (d, 1H), 7.82 (m, 2H), 7.59 (m, 3H), 5.23 (s, 2H), 4.29 (q, 2H), 3.38 (s, 3H) 10-166 4-Cl—Ph Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.76 (s, 1H), 8.11 (d, 1H), 7.95 (d, 1H), 7.83 (d, 2H), 7.65 (d, 2H), 5.25 (s, 2H), 4.28 (q, 2H), 3.36 (s, 3H) 10-167 1-ethylbenz- Cl CH₂OCH₂CF₃ SO₂Me imidazol-2-yl 10-168 1,2,4-triazol-1-yl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.99 (s, 1H), 9.34 (s, 1H), 8.47 (s, 1H), 8.14 (d, 1H), 7.95 (d, 1H), 5.24 (s, 2H), 4.29 (q, 2H), 3.38 (s, 3H) 10-169 benzoxazol-2-yl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d6, 400 MHz 11.96 (s, 1H), 8.23 (d, 1H), 8.08 (d, 1H), 8.02 (d, 1H), 7.95 (d, 1H),7.62 (dd, 1H), 7.54 (dd, 1H), 5.27 (s, 2H), 4.30 (q, 2H), 3.38 (s, 3H) 10-170 Ph Cl 5-cyano- SO₂Et methyl-4,5- dihydro-1,2- oxazol-3-yl 10-171 4-Cl—Ph Cl 5-cyano- SO₂Et ¹H NMR, CDCl₃, 400 MHz methyl-4,5- 8.51 (bs, 1H), 8.08 (d, dihydro-1,2- 1H), 7.70 (m, 3H), 7.51 oxazol-3-yl (d, 2H), 5.15 (s, 2H), 4.03 (m, 1H), 3.81-3.57 (m, 4H), 3.26 (s, 3H), 2.00-1.80 (m, 3H), 1.58 (m, 1H) 10-172 1-ethyl- Cl 5-cyano- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz benzimidazol-2-yl methyl-4,5- 11.92 (bs, 1H), 8.26 (s, dihydro-1,2- 2H), 7.84 (m, 2H), 7.46 oxazol-3-yl (dd, 1H), 7.37 (dd, 1H), 5.20 (m, 1H), 4.68 (m, 2H), 3.61 (dd, 1H), 3.46 (q, 2H), 3.19 (dd, 1H), 3.01 (m, 2H), 1.42 (t, 3H), 1.18 (t, 3H) 10-173 1,2,4-triazol-1-yl Cl 5-cyano- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz methyl-4,5- 12.01 (s, 1H), 9.35 (s, dihydro-1,2- 1H), 8.47 (s, 1H), 8.15 oxazol-3-yl (d, 1H), 8.08 (d, 1H), 5.19 (m, 1H), 3.60 (dd, 1H), 3.41 (q, 2H), 3.17 (dd, 1H), 3.00 (m, 2H), 1.16 (t, 3H) 10-174 benzoxazol-2-yl Cl 5-cyano- SO₂Et ¹H-NMR, DMSO-d₆, 400 MHz methyl-4,5- 12.08 (bs, 1H), 8.23 (m, dihydro-1,2- 2H), 8.00 (m, 2H), 7.49 oxazol-3-yl (m, 2H), 5.20 (m, 1H), 3.70-2.90 (m, 6H), 1.19 (t, 3H) 10-175 Ph Cl CH₂O-tetra- SO₂Me hydrofuran-3-yl 10-176 4-Cl—Ph Cl CH₂O-tetra- SO₂Me hydrofuran-3-yl 10-177 1-ethyl- Cl CH₂O-tetra- SO₂Me benzimidazol-2-yl hydrofuran-3-yl 10-178 1,2,4-triazol-1-yl Cl CH₂O-tetra- SO₂Me hydrofuran-3-yl 10-179 benzoxazol-2-yl Cl CH₂O-tetra- SO₂Me hydrofuran-3-yl 10-180 Ph Cl CH₂O-tetra- SO₂Me hydrofuran-2-yl 10-181 Ph Cl SMe SO₂Me 10-182 Ph Cl F SMe 10-183 1,2,4-triazol-1-yl Cl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydro- 11.95 (bs, 1H), 9.34 (s, furan-2-yl 1H), 8.49 (s, 1H), 8.12 (d, 1H), 7.91 (d, 1H), 5.18 (s, 2H), 3.97 (m, 1H), 3.71 (dd, 1H), 3.68- 3.51(m, 3H), 3.40 (s, 3H), 1.94-1.43 (m, 4 H) 10-184 1-ethyl- Cl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz benzimidazol-2-yl tetrahydro- 11.92 (bs, 1H), 8.21 (d, furan-2-yl 1H), 8.10 (d, 1H), 7.82 (dd, 2H), 7.46 (dd, 1H), 7.35 (dd, 1H), 5.21 (s, 2H), 4.47 (q, 2H), 3.98 (m, 1H), 3.72 (dd, 1H), 3.66-3.52 (m, 3H), 3.42 (s, 3H), 1.90 (m, 1H), 1.77 (m, 2H), 1.55 (m, 1H), 1.42 (t, 3 H) 10-185 Ph Cl CH₂OCH₂- SO₂Me tetrahydro- furan-3-yl 10-186 Ph Cl O(CH₂)-5- Cl pyrrolidin-2- one 10-187 Ph Cl SMe Cl 10-188 Ph Cl S(O)Me Cl 10-189 Ph Cl SO₂Me Cl 10-190 Ph Cl CH₂O- SO₂Et tetrahydro- furan-3-yl 10-191 Ph Cl O(CH₂)₂OMe Cl 10-192 4-Cl—Ph Cl O(CH₂)₂OMe Cl 10-193 1-ethyl- Cl O(CH₂)₂OMe Cl benzimidazol-2-yl 10-194 1,2,4-triazol-1-yl Cl O(CH₂)₂OMe Cl 10-195 benzoxazol-2-yl Cl O(CH₂)₂OMe Cl 10-196 Ph Cl O(CH₂)₄OMe SO₂Me 10-197 Ph Cl O(CH₂)₄OMe SO₂Et 10-198 Ph Cl O(CH₂)₃OMe SO₂Me 10-199 Ph Cl O(CH₂)₃OMe SO₂Et 10-200 Ph Cl O(CH₂)₂OMe SO₂Me 10-201 Ph Cl O(CH₂)₂OMe SO₂Et 10-202 Ph Cl [1,4]dioxan-2- SO₂Me ylmethoxy 10-203 Ph Cl [1,4]dioxan-2- SO₂Et ylmethoxy 10-204 Ph Cl SO₂Me Me 10-205 Ph Cl SEt Me 10-206 Ph Cl SOEt Me 10-207 Ph Cl SO₂Et Me 10-208 Ph Cl 4,5-dihydro- SO₂Me 1,2-oxazol-3-yl 10-209 Ph Cl Cl SO₂Me 10-210 Ph F SMe CF₃ 10-211 4-Cl—Ph F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 9.12 (s, 1H), 8.76 (dd, 1H), 7.75 (dd, 1H), 7.67 (d, 2H), 7.49 (d, 2H), 3.12 (s, 3H) 10-212 Ph F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 9.19 (bs, 1H), 8.26 (dd, 1H), 7.71 (d, 1H), 7.67 (d, 2H), 7.50 (d, 2H), 3.13 (s, 3H) 10-213 Ph OMe SMe CF₃ 10-214 Ph OMe S(O)Me CF₃ 10-215 Ph OMe SO₂Me CF₃ 10-216 Ph Et NH(CH₂)₂OMe SO₂Me 10-217 Ph Et F SO₂Me 10-218 Ph Et SMe CF₃ 10-219 Ph CF₃ F SO₂Me 10-220 Ph CF₃ F SO₂Et 10-221 Ph CF₃ O(CH₂)₂OMe SO₂Et 10-222 Ph CF₃ O(CH₂)₃OMe SO₂Et 10-223 Ph CF₃ O(CH₂)₂OMe SO₂Me 10-224 Ph CF₃ O(CH₂)₃OMe SO₂Me 10-225 Ph CF₃ OCH₂CONMe₂ SO₂Me 10-226 Ph CF₃ OCH₂CONMe₂ SO₂Et 10-227 Ph CF₃ OCH₂CONMe₂ Cl 10-228 Ph CF₃ OCH₂CONMe₂ Br 10-229 Ph CF₃ OCH₂CONMe₂ I 10-230 Ph CF₃ OCH₂CONMe₂ F 10-231 Ph CF₃ O(CH₂)₂OMe Cl 10-232 Ph CF₃ O(CH₂)₃OMe Cl 10-233 Ph CF₃ O(CH₂)₂OMe Br 10-234 Ph CF₃ O(CH₂)₃OMe Br 10-235 Ph CF₃ O(CH₂)₂OMe I 10-236 Ph CF₃ O(CH₂)₃OMe I 10-237 Ph CF₃ O(CH₂)₂OMe F 10-238 Ph CF₃ O(CH₂)₃OMe F 10-239 Ph CF₃ [1,4]dioxan-2- SO₂Me ylmethoxy 10-240 Ph CF₃ [1,4]dioxan-2- SO₂Et ylmethoxy 10-241 Ph CF₃ [1,4]dioxan-2- Cl ylmethoxy 10-242 Ph CF₃ [1,4]dioxan-2- Br ylmethoxy 10-243 Ph CF₃ [1,4]dioxan-2- I ylmethoxy 10-244 Ph CF₃ [1,4]dioxan-2- F ylmethoxy 10-245 Ph Br OMe Br 10-246 Ph Br O(CH₂)₂OMe Br 10-247 Ph Br O(CH₂)₄OMe SO₂Me 10-248 Ph Br O(CH₂)₄OMe SO₂Et 10-249 Ph Br O(CH₂)₃OMe SO₂Me 10-250 Ph Br O(CH₂)₃OMe SO₂Et 10-251 Ph Br O(CH₂)₂OMe SO₂Me 10-252 Ph Br O(CH₂)₂OMe SO₂Et 10-253 Ph Br [1,4]dioxan-2- SO₂Me ylmethoxy 10-254 Ph Br [1,4]dioxan-2- SO₂Et ylmethoxy 10-255 Ph Br SMe Me 10-256 Ph Br SOMe Me 10-257 Ph Br SO₂Me Me 10-258 Ph Br SEt Me 10-259 Ph Br SOEt Me 10-260 Ph Br SO₂Et Me 10-261 Ph I O(CH₂)₄OMe SO₂Me 10-262 Ph I O(CH₂)₄OMe SO₂Et 10-263 Ph I O(CH₂)₃OMe SO₂Me 10-264 Ph I O(CH₂)₃OMe SO₂Et 10-265 Ph I O(CH₂)₂OMe SO₂Me 10-266 Ph I O(CH₂)₂OMe SO₂Et 10-267 Ph I [1,4]dioxan-2- SO₂Me ylmethoxy 10-268 Ph I [1,4]dioxan-2- SO₂Et ylmethoxy 10-269 Ph I SMe Me 10-270 Ph I SOMe Me 10-271 Ph I SO₂Me Me 10-272 Ph I SEt Me 10-273 Ph I SOEt Me 10-274 Ph I SO₂Et Me 10-275 Ph CH₂SMe OMe SO₂Me 10-276 Ph CH₂OMe OMe SO₂Me 10-277 Ph CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 10-278 Ph CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 10-279 Ph CH₂O(CH₂)₃OMe OMe SO₂Me 10-280 Ph CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 10-281 Ph CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 10-282 Ph SO₂Me NH₂ CF₃ 10-283 Ph SO₂Me F CF₃ 10-284 Ph SO₂Me NHEt Cl 10-285 Ph SMe SEt F 10-286 Ph SMe SMe F 10-287 5-phenyl-1H- Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 1,2,3-triazol-1-yl 12.21 (s, 1H), 8.32 (s, 1H), 8.02 (d, 1H), 7.70 (d, 1H), 7.53 (m, 5H), 3.40 (s, 3H), 2.58 (s, 3H). 10-288 5-phenyl-1H- Me SO₂Me SO₂Me 1,2,3-triazol-1-yl 10-289 4-OMe-phenyl Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.51 (s, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.76 (d, 2H), 7.14 (m, 2H), 3.83 (s, 3H), 3.41 (s, 3H), 2.28 (s, 3H) 10-290 4-OMe-phenyl Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 8.26 (d, 1H), 8.05 (d, 1H), 7.72 (d, 2H), 7.13 (d, 2H), 3.83 (s, 3H), 3.51 (s, 3H), 3.47 (s, 3H), 2.64 (s, 3H) 10-291 4-OMe-phenyl Me S(O)Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.49 (s, 1H), 7.87 (broad, 2H), 7.94 (d, 1H), 7.75 (m, 2H), 7.15 (m, 2H), 3.83 (s, 3H), 3.04 (s, 3H), 2.80 (s, 3H) 10-292 4-OMe-phenyl Cl 5-cyano- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz methyl-4,5- 11.67 (s, 1H), 8.13 (d, dihydro-1,2- 1H), 8.08 (d, 1H), 7.75 oxazol-3-yl (m, 2H), 7.77 (m, 2H), 7.14 (m, 2H), 5.20 (m, 1H), 3.84 (s, 3H), 3.61 (dd, 1H), 3.43 (q, 2H), 3.17 (dd, 1H), 1.17 (t, 3H) 10-293 4-OMe-phenyl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.63 (s, 1H), 8.13 (d, 1H), 7.95 (d, 1H), 7.78 (m, 2H), 7.13 (m, 2H), 5.25 (s, 2H), 4.29 (q, 2H), 3.84 (s, 3H), 3.36 (s, 3H) 10-293 4-OMe-phenyl Cl Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.50 (s, 1H), 8.06 (d, 1H), 7.80 (d, 1H), 7.75 (m, 2H), 7.14 (m, 2H), 3.83 (s, 3H), 3.43 (s, 3H), 2.41 (s, 3H) 10-294 4-Cl—Ph Cl CH₂OCH₂- SO₂Me ¹H NMR, CDCl₃, 400 MHz tetrahydro- 8.06 (d, 1H), 7.71 (m, furan-2-yl 3H), 7.50 (m, 2H), 5.16 (s, 2H), 4.02 (m, 1H), 3.81-3.57 (m, 4H), 3.25 (s, 3H), 1.99-1.83 (m, 3H) 10-295 4-Cl—Ph Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.62 (s, 1H), 8.05 (d, 1H), 7.80 (m, 3H), 7.66 (m, 2H), 7.14 (m, 2H), 3.43 (s, 3H), 2.40 (s, 3H) 10-296 4-Cl—Ph Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.62 (s, 1H), 7.87 (s, 2H), 7.82 (d, 2H), 7.66 (d, 2H), 3.04 (s, 3H), 2.79 (s, 3H) 10-297 4-F—Ph Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.59 (s, 1H), 8.04 (d, 1H), 7.98 (d, 1H), 7.85 (m, 2H), 7.45 (m, 2H), 3.40 (s, 3H), 2.64 (s, 3H) 10-298 4-F—Ph Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.60 (s, 1H), 8.28 (d, 1H), 8.08 (d, 1H), 7.85 (m, 2H), 7.44 (m, 2H), 3.59 (s, 3H), 3.47 (s, 3H), 2.62 (s, 3H) 10-299 4-F—Ph Cl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydro- 11.70 (s, 1H), 8.09 (d, furan-2-yl 1H), 7.86 (m, 3H), 7.44 (t, 2H), 5.07 (s, 2H), 3.97 (m, 1H), 3.58 (dd, 1H), 3.65-3.51 (m, 3H), 3.39 (s, 3H), 1.95-1.72 (m, 3H), 1.53 (m, 1H) 10-300 4-F—Ph Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.71 (s, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.86 (dd, 2H), 7.43 (dd, 2H), 5.24 (s, 2H), 4.29 (q, 2H), 3.36 (s, 3H) 10-301 4-F—Ph Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.45 (s, 1H), 7.92 (d, 1H), 7.85 (m, 2H), 7.61 (d, 1H), 7.43 (dd, 2H), 3.26 (s, 3H), 2.61 (s, 3H), 2.27 (s, 3H) 10-302 4-F—Ph Cl 5-cyano- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz methyl-4,5- 11.78 (s, 1H), 8.10 (dd, dihydro-1,2- 2H), 7.87 (m, 2H), 7.44 oxazol-3-yl (dd, 2H), 5.19 (m, 1H), 3.59 (dd, 1H), 3.43 (q, 2H), 3.15 (dd, 1H), 3.01 (m, 2H), 1.16 (t, 3H) 10-304 4-F—Ph Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.58 (s, 1H), 7.85 (m, 4H), 7.44 (m, 2H), 3.04 (s, 3H), 2.78 (s, 3H) 10-305 Ph Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 11.64 (s, 1H), 8.01 (d, 1H), 7.80 (m, 2H), 7.75 (d, 1H), 7.59 (m, 3H), 3.42 (q, 2H), 2.73 (s, 3H), 1.13 (t, 3H) 10-306 Ph Me 1,2,3-1H- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz triazol-1-yl 11.72 (s, 1H), 8.53 (s, 1H), 8.17 (d, 1H), 8.12 (d, 1H), 8.05 (s, 1H), 7.79 (m, 2H), 7.57 (m, 2H), 3.13 (s, 3H), 1.81 (s, 3H) 10-307 1,2,4-triazol-1-yl Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.87 (s, 1H), 9.39 (s, 1H), 8.48 (s, 1H), 7.90 (d, 1H), 7.88 (d, 1H), 3.05 (s, 3H), 2.85 (s, 3H) 10-308 4-methyl-1,3- Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz thiazol-2-yl 11.65 (s, 1H), 8.10 (2d, 2H), 7.71 (s, 1H), 3.44 (s, 3H), 2.82 (s, 3H) 10-309 thiophen-2-yl Me SO₂Me CF₃ 10-310 1,2,4-oxadiazol-3-yl Me SO₂Me CF₃ 10-311 5-methoxymethyl- Me SO₂Me CF₃ 1,2,4-oxadiazol-3-yl 10-312 1-methyl-5- Me SO₂Me CF₃ ethylsulfonyl- 1,3,4-triazol-2-yl 10-313 4-methyl-1,3- Me SO₂Me SO₂Me thiazol-2-yl 10-314 thiophen-2-yl Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.60 (s, 1H), 8.30 (d, 1H), 8.15 (d, 1H), 7.94 (d, 1H), 7.77 (d, 1H), 7.31 (dd, 1H), 3.61 (s, 3H), 3.57 (s, 1H), 2.71 (s, 3H) 10-315 1,2,4-oxadiazol-3-yl Me SO₂Me SO₂Me 10-316 5-methoxymethyl- Me SO₂Me SO₂Me 1,2,4-oxadiazol-3-yl 10-317 1-methyl-5- Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz methylsulfonyl- 11.89 (s, 1H), 8.08 (d, 1,3,4-triazol-2-yl 1H), 7.99 (d 1H), 4.08 (s, 3H), 3.66 (s, 3H), 3.42 (s, 3H), 2.72 (s, 3H) 10-318 pyridin-2-yl Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.62 (s, 1H), 8.74 (d, 1H), 8.13-8.05 (m, 4H), 7.63 (dd, 1H), 3.43 (s, 1H), 2.78 (s, 3H) 10-319 pyridin-2-yl Me S(O)Me CF₃ 10-320 pyridin-2-yl Me SO₂Me SO₂Me 10-321 pyridin-3-yl Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.74 (s, 1H), 8.98 (bs, 1H), 8.78 (bd, 1H), 8.21 (dd, 1H), 8.04 (d, 1H), 8.02 (d, 1H), 7.63 (dd, 1H), 3.41 (s, 3H), 2.66 (s, 3H) 10-322 pyridin-3-yl Me S(O)Me CF₃ 10-323 pyridin-3-yl Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.74 (s, 1H), 8.96 (d, 1H), 8.77 (dd, 1H), 8.27 (d, 1H), 8.21 (dt, 1H), 8.07 (d, 1H), 7.62 (dd, 1H), 3.59 (s, 3H), 3.54 (s, 3H), 2.62 (s, 3H) 10-324 pyridin-4-yl Me SO₂Me CF₃ 10-325 pyridin-4-yl Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.82 (s, 1H), 8.85 (m, 2H), 7.88 (m, 4H), 3.04 (s, 3H), 2.79 (s, 3H) 10-326 pyridin-4-yl Me SO₂Me SO₂Me 10-327 4-(5-allylsulfanyl)- Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 4-methyl-4H- 11.52 (s, 1H), 8.09 (d, 1,2,4-triazol-3-yl 1H), 8.03 (d 1H), 5.95 (m, 1H), 5.24 (dd, 1H), 5.10 (dd, 1H), 3.88 (d, 2H), 3.43 (s, 3H), 2.74 (s, 3H) 10-328 4-(5-allylsulfanyl)- Me S(O)Me CF₃ 4-methyl-4H- 1,2,4-triazol-3-yl 10-329 4-(5-allylsulfanyl)- Me SO₂Me SO₂Me 4-methyl-4H- 1,2,4-triazol-3-yl

TABLE 11 Compounds of the general formula (I) according to the invention (I)

No. R X Y Z Physical data 11-2 Bz CF₃ SMe SO₂Me 11-3 Bz CF₃ OCH₂(CO)NMe₂ SO₂Me 11-4 Bz Cl pyrazol-1-yl SO₂Me 11-5 Bz Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 10.13 (s, 1H), 8.44 (d, 2H), 8.25 (d, 1H), 7.90 (d, 1H), 7.76 (t, 1H), 7.60 (t, 2H), 5.42 (s, 2H), 4.08 (q, 2H), 3.26 (s, 3H) 11-6 Bz Cl CH₂O-tetra- SO₂Me hydrofuran-3-yl 11-7 Bz Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-8 Bz Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-9 Bz Me SO₂Me Cl 11-10 Bz Me SO₂Me SO₂Me 11-11 Bz Me SO₂Me CF₃ 11-12 Bz Me NMe₂ SO₂Me 11-13 Bz Cl O(CH₂)₂OMe Cl 11-14 Bz Me NH(CH₂)₂OMe SO₂Me 11-15 Bz Me O(CH₂)₂NHSO₂Me SO₂Me 11-16 CO₂Me CF₃ SMe SO₂CH₃ 11-17 CO₂Me CF₃ OCH₂(CO)NMe₂ SO2Me 11-18 CO₂Me Cl pyrazol-1-yl SO2Me 11-19 CO₂Me F SO₂Me CF₃ 11-20 CO₂Me Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 9.55 (bs, 1H), 8.22 (d, 1H), 7.88 (d, 1H), 5.39 (s, 2H), 4.08 (m, 5H), 3.25 (s, 3H) 11-21 CO₂Me Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-22 CO₂Me Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, CDCl³, 400 MHz dihydro-1,2-oxazol- 9.68 (bs, 1H), 8.18 (d, 1H), 8.03 (d, 1H), 3-yl 5.19 (m, 1H), 4.10 (s, 3H), 3.75 (m, 1H), 3.39 (q, 2H), 3.30 (m, 1H), 2.82-3.02 (m, 2H), 1.32 (t, 3H) 11-23 CO₂Me Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-24 CO₂Me Me SO₂Me Cl 11-25 CO₂Me Me SO₂Me SO₂Me 11-26 CO₂Me Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.13 (s, 1H), 8.06 (d, 1H), 7.97 (d, 1H), 3.95 (s, 3H), 3.41 (s, 3H), 2.75 (s, 3H) 11-27 CO₂Me Me NMe₂ SO₂Me 11-28 CO₂Me Cl O(CH₂)₂OMe Cl 11-29 CO₂Me Me NH(CH₂)₂OMe SO₂Me 11-30 CO₂Me Me O(CH₂)₂NHSO2Me SO₂Me 11-31 NHAc CF3 SMe SO₂CH₃ 11-32 NHAc CF3 OCH₂(CO)NMe₂ SO₂Me 11-33 NHAc Cl pyrazol-1-yl SO₂Me 11-34 NHAc F SO₂Me CF₃ 11-35 NHAc Cl CH₂OCH₂CF₃ SO₂Me 11-36 NHAc Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-37 NHAc Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-38 NHAc Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-39 NHAc Me SO₂Me Cl 11-40 NHAc Me SO₂Me SO₂Me ¹H-NMR, DMSO-d₆, 400 MHz 11.41 (s, 1H), 10.85 (s, 1H), 8.28 (d, 1H), 8.03 (d, 1H), 6.14 (bs, 2H), 3.60 (s, 3H), 3.57 (s, 3H), 2.70 (s, 3H), 2.09 (s, 3H) 11-41 NHAc Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.40 (s, 1H), 10.85 (s, 1H), 8.07 (d, 1H), 7.99 (d, 1H), 3.42 (s, 3H), 2.76 (s, 3H), 2.09 (s, 3H) 11-42 NHAc Me NMe₂ SO₂Me 11-43 NHAc Cl O(CH₂)₂OMe Cl 11-44 NHAc Me NH(CH₂)₂OMe SO₂Me 11-45 NHAc Me O(CH₂)₂NHSO₂Me SO₂Me 11-46 Ac CF₃ SMe SO₂CH₃ 11-47 Ac CF₃ OCH₂(CO)NMe₂ SO₂Me 11-48 Ac Cl pyrazol-1-yl SO₂Me 11-49 Ac F SO₂Me CF₃ 11-50 Ac Cl CH₂OCH₂CF₃ SO₂Me 11-51 Ac Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-52 Ac Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-53 Ac Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-54 Ac Me SO₂Me Cl 11-55 Ac Me SO₂Me SO₂Me 11-56 Ac Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.76 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 3.43 (s, 3H), 2.74 (s, 3H), 2.71 (s, 3H) 11-57 Ac Me NMe₂ SO₂Me 11-58 Ac Cl O(CH₂)₂OMe Cl 11-59 Ac Me NH(CH₂)₂OMe SO₂Me 11-60 Ac Me O(CH₂)₂NHSO₂Me SO₂Me 11-61 piperidin- CF₃ SMe SO₂CH₃ 1-yl 11-62 piperidin- CF₃ OCH₂(CO)NMe₂ SO₂Me 1-yl 11-63 piperidin- Cl Pyrazol-1-yl SO₂Me 1-yl 11-64 piperidin- F SO₂Me CF₃ 1-yl 11-65 piperidin- Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.31 (s, 1H), 8.11 (d, 1H), 7.89 (d, 1H), 5.24 (s, 2H), 4.29 (q, 2H), 3.36 (s, 3H), 1.59 (bs, 6H) 11-66 piperidin- Cl CH₂O- SO₂Me 1-yl tetrahydrofuran-3-yl 11-67 piperidin- Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, CDCl₃, 400 MHz 1-yl dihydro-1,2-oxazol- 8.13 (broad d, 1H), 7.95 (broad, 1H), 5.17 3-yl (m, 2H), 3.71 (m, 1H), 3.39-3.20 (m, 6H), 2.90 (m, 2H), 1.68 (broad, 6H), 1.27 (t, 3H) 11-68 piperidin- Me 4,5-dihydro-1,2- SO₂Me 1-yl oxazol-3-yl 11-69 piperidin- Me SO₂Me Cl 1-yl 11-70 piperidin- Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.20 (s, 1H), 8.29 (d, 1H), 7.99 (d, 1H), 3.60 (s, 3H), 3.57 (s, 3H), 3.31 (broad, 4H), 2.70 (s, 3H), 1.61 (bs, 6H) 11-71 piperidin- Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.19 (s, 1H), 8.04 (d, 1H), 7.93 (d, 1H), 3.43 (s, 3H), 3.29 (m, 4H), 2.74 (s, 3H), 1.60 (broad, 6H) 11-72 piperidin- Me NMe₂ SO₂Me 1-yl 11-73 piperidin- Cl O(CH₂)₂OMe Cl 1-yl 11-74 SMe CF₃ SMe SO₂CH₃ 11-75 SMe CF₃ OCH₂(CO)NMe₂ SO₂Me 11-76 SMe Cl pyrazol-1-yl SO₂Me 11-77 SMe F SO₂Me CF₃ 11-78 SMe Cl CH₂OCH₂CF₃ SO₂Me 11-79 SMe Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-80 SMe Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-81 SMe Me 4,5-dihydro-1,2- SO₂Me oxazol-3 yl 11-82 SMe Me SO₂Me Cl 11-83 SMe Me SO₂Me SO₂Me 11-84 SMe Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.80 (s, 1H), 8.05 (d, 1H), 7.96 (d, 1H), 3.42 (s, 3H), 2.76 (s, 3H), 2.66 (s, 3H) 11-85 SMe Me NMe₂ SO₂Me 11-86 SMe Cl O(CH₂)₂OMe Cl 11-87 SMe Me NH(CH₂)₂OMe SO₂Me 11-88 SMe Me O(CH₂)₂NHSO₂Me SO₂Me 11-89 Cl CF₃ SMe SO₂CH₃ 11-90 Cl CF₃ OCH₂(CO)NMe₂ SO₂Me 11-91 Cl Cl pyrazol-1-yl SO₂Me 11-92 Cl F SO₂Me CF₃ 11-93 Cl Cl CH₂OCH₂CF₃ SO₂Me 11-94 Cl Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-95 Cl Cl 5-cyanomethyl- SO₂Et dihydro-1,2-oxazol- 3-yl 11-96 Cl Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-97 Cl Me SO₂Me Cl 11-98 Cl Me SO₂Me SO₂Me 11-99 Cl Me SO₂Me CF₃ 11-100 Cl Me NMe₂ SO₂Me 11-101 Cl Cl O(CH₂)₂OMe Cl 11-102 Cl Me NH(CH₂)₂OMe SO₂Me 11-103 Cl Me O(CH₂)₂NHSO₂Me SO₂Me 11-104 Br CF₃ SMe SO₂CH₃ 11-105 Br CF₃ OCH₂(CO)NMe₂ SO₂Me 11-106 Br Cl pyrazol-1-yl SO₂Me 11-107 Br F SO₂Me CF₃ 11-108 Br Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.86 (s, 1H), 8.13 (d, 1H), 7.94 (d, 1H), 5.26 (s, 2H), 4.30 (q, 2H), 3.37 (s, 3H) 11-109 Br Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-110 Br Cl 5-cyanomethyl- SO₂Et dihydro-1,2-oxazol- 3-yl 11-111 Br Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-112 Br Me SO₂Me Cl 11-113 Br Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.76 (s, 1H), 8.27 (d, 1H), 7.05 (d, 1H), 3.60 (s, 3H), 3.57 (s, 3H), 2.73 (s, 3H) 11-114 Br Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.74 (s, 1H), 8.05 (d, 1H), 7.99 (d, 1H), 3.43 (s, 3H), 2.76 (s, 3H) 11-115 Br Me NMe₂ SO₂Me 11-116 Br Cl O(CH₂)₂OMe Cl 11-117 Br Me NH(CH₂)₂OMe SO₂Me 11-118 Br Me O(CH₂)₂NHSO₂Me SO₂Me 11-119 I CF₃ SMe SO₂CH₃ 11-120 I CF₃ OCH₂(CO)NMe₂ SO₂Me 11-121 I Cl pyrazol-1-yl SO₂Me 11-122 I F SO₂Me CF₃ 11-123 I Cl CH₂OCH₂CF₃ SO₂Me 11-124 I Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-125 I Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-126 I Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-127 I Me SO₂Me Cl 11-128 I Me SO₂Me SO₂Me 11-129 I Me SO₂Me CF₃ 11-130 I Me NMe₂ SO₂Me 11-131 I Cl O(CH₂)₂OMe Cl 11-132 I Me NH(CH₂)₂OMe SO₂Me 11-133 I Me O(CH₂)₂NHSO₂Me SO₂Me 11-134 C(O)NH2 CF₃ SMe SO₂CH₃ 11-135 C(O)NH2 CF₃ OCH₂(CO)NMe₂ SO₂Me 11-136 C(O)NH2 Cl pyrazol-1-yl SO₂Me 11-137 C(O)NH2 F SO₂Me CF₃ 11-138 C(O)NH2 Cl CH₂OCH₂CF₃ SO₂Me 11-139 C(O)NH2 Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-140 C(O)NH2 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-141 C(O)NH2 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-142 CH₂OMe Me SO₂Me Cl 11-143 CH₂OMe Me SO₂Me SO₂Me 11-144 CH₂OMe Me SO₂Me CF₃ 11-145 CH₂OMe Me NMe₂ SO₂Me 11-146 CH₂OMe Cl O(CH₂)₂OMe Cl 11-147 CH₂OMe Me NH(CH₂)₂OMe SO₂Me 11-148 CH₂OMe Me O(CH₂)₂NHSO₂Me SO₂Me 11-149 NH₂ CF₃ SMe SO₂CH₃ 11-150 NH₂ CF₃ OCH₂ (CO)NMe₂ SO₂Me 11-151 NH₂ Cl pyrazol-1-yl SO₂Me 11-152 NH₂ Me 1,2,3-triazol-2-yl SO₂Me 11-153 NH₂ Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.32 (s, 1H), 8.13 (d, 1H), 8.05 (d, 1H), 6.13 (bs, 2H), 5.25 (s, 2H), 4.30 (q, 2H), 3.36 (s, 3H) 11-154 NH₂ Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-155 NH₂ Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz dihydro-1,2-oxazol- 11.35 (s, 1H), 8.18 (d, 1H), 8.15 (d, 1H), 3-yl 6.14 (bs, 2H), 5.20 (m, 1H), 3.60 (dd, 1H), 3.42 (q, 2H), 3.17 (dd, 1H), 3.02 (m, 2H), 1.17 (t, 3H) 11-156 NH₂ Me 4,5-dihydro-1,2- SO₂Me oxazol-3 yl 11-157 NH₂ Me SO₂Me Cl 11-158 NH₂ Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.02 (s, 1H), 8.14 (d, 1H), 7.89 (d, 1H), 6.12 (bs, 2H), 3.42 (s, 3H), 2.73 (s, 3H) 11-159 NH₂ Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.20 (s, 1H), 8.10 (d, 1H), 8.06 (d, 1H), 6.15 (bs, 2H), 3.60 (s, 3H), 3.58 (s, 3H), 2.67 (s, 3H) 11-160 NH₂ Me NMe₂ SO₂Me 11-161 NH₂ Cl O(CH₂)₂OMe Cl 11-162 NH₂ Me NH(CH₂)₂OMe SO₂Me 11-163 NH₂ Me O(CH₂)₂NHSO₂Me SO₂Me 11-164 H CF₃ SMe SO₂CH₃ 11-165 H CF₃ OCH₂(CO)NMe₂ SO₂Me 11-166 H Cl pyrazol-1-yl SO₂Me 11-167 H F SO₂Me CF₃ 11-168 H Cl CH₂OCH₂CF₃ SO₂Me 11-169 H Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-170 H Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-171 H Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-172 H Me SO₂Me Cl 11-173 H Me SO₂Me SO₂Me 11-174 H Me SO₂Me CF₃ 11-175 H Me NMe₂ SO₂Me 11-176 H Cl O(CH₂)₂OMe Cl 11-177 H Me NH(CH₂)₂OMe SO₂Me 11-178 H Me O(CH₂)₂NHSO₂Me SO₂Me 11-179 NO₂ CF₃ SMe SO₂CH₃ 11-180 NO₂ CF₃ OCH₂(CO)NMe₂ SO₂Me 11-181 NO₂ Cl pyrazol-1-yl SO₂Me 11-182 NO₂ F SO₂Me CF₃ 11-183 NO₂ Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 9.48 (broad s, 1H), 8.13 (d, 1H), 7.87 (d, 1H), 5.34 (s, 2H), 4.08 (q, 2H), 3.32 (s, 3H) 11-184 NO₂ Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-185 NO₂ Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz dihydro-1,2-oxazol- 12.26 (s, 1H), 8.15 (d, 1H), 8.01 (d, 1H), 3-yl 5.20 (m, 1H), 3.61 (dd, 1H), 3.44 (q, 2H), 3.17 (dd, 1H), 3.03 (m, 2H), 1.18 (t, 3H) 11-186 NO₂ Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-187 NO₂ Me SO₂Me Cl 11-188 NO₂ Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.28 (s, 1H), 8.29 (d, 1H), 8.02 (d, 1H), 3.61 (s, 3H), 3.58 (s, 3H), 2.70 (s, 3H) 11-189 NO₂ Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.30 (s, 1H), 8.09 (d, 1H), 7.93 (d, 1H), 3.44 (s, 3H), 2.72 (s, 3H) 11-190 NO₂ Me NMe₂ SO₂Me 11-191 NO₂ Cl O(CH₂)₂OMe Cl 11-192 NO₂ Me NH(CH₂)₂OMe SO₂Me 11-193 NO₂ Me O(CH₂)₂NHSO2Me SO₂Me 11-194 c-Pr CF₃ SMe SO₂CH₃ 11-195 c-Pr CF₃ OCH₂(CO)NMe2 SO₂Me 11-196 c-Pr Cl pyrazol-1-yl SO₂Me 11-197 c-Pr F SO₂Me CF₃ 11-198 c-Pr Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.64 (s, 1H), 8.13 (d, 1H), 7.99 (d, 1H), 5.24 (s, 2H), 4.30 (q, 2H), 3.37 (s, 3H), 2.09 (m, 1H), 1.14 (m, 2H), 0.97 (m, 2H) 11-199 c-Pr Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 11-200 c-Pr Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 11-201 c-Pr Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 11-202 c-Pr Me SO₂Me Cl 11-203 c-Pr Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.55 (s, 1H), 8.28 (d, 1H), 8.08 (d, 1H), 3.60 (s, 3H), 3.57 (s, 3H), 2.72 (s, 3H), 2.06 (m, 1H), 1.13 (m, 2H), 0.95 (m, 2H) 11-204 c-Pr Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.53 (s, 1H), 8.04 (s, 2H), 3.43 (s, 3H), 2.76 (s, 3H), 2.07 (m, 1H), 1.12 (m, 2H), 0.96 (m, 2H) 11-205 c-Pr Me NMe₂ SO₂Me 11-206 c-Pr Cl O(CH₂)₂OMe Cl 11-207 c-Pr Me NH(CH₂)₂OMe SO₂Me 11-208 c-Pr Me O(CH₂)₂NHSO₂Me SO₂Me 11-209 piperidin- Cl SMe SO₂Me 1-yl 11-210 piperidin- F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 1-yl 8.78 (broad, 1H), 8.35 (bs, 1H), 7.75 (d, 1H), 3.29 (bs, 4H), 3.14 (s, 1H), 1.75- 1.61(m, 6H) 11-211 piperidin- Cl (tetrahydrofuran-2- SO₂Me ¹H NMR, CDCl₃, 400 MHz 1-yl ylmethoxy)methyl 8.11 (d, 1H), 7.60 (d, 1H), 5.14 (m, 2H), 4.09 (m, 1H), 3.86-3.68 (m, 2H), 3.65- 3.54 (m, 2H), 3.30 (s, 3H), 2.02-1.81 (m, 4H), 1.74-1.50 (m, 4H), 1.69 (m, 3H), 1.58 (m, 2H) 11-212 piperidin- Cl Me SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.22 (s, 1H), 8.03 (d, 1H), 7.68 (d, 1H), 3.41 (q, 2H), 3.31 (m, 4H), 2.72 (s, 3H), 1.59 (broad, 6H), 1.12 /t, 3H) 11-213 piperidin- Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.04 (s, 1H), 7.94 (d, 1H), 7.53 (d, 1H), 3.29 (s, 3H), 2.63 (s, 3H), 2.36 (s, 3H) 11-214 piperidin- Cl Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.15 (s, 1H), 8.05 (d, 1H), 7.72 (d, 1H), 3.43 (s, 3H), 3.28 (broad, 4H), 1.59 (bs, 6H) 11-215 piperidin- Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl SO₂Me 11.10 (s, 1H), 8.06 (d, 1H), 7.84 (d, 1H), 3.42 (s, 3H), 3.31 (broad, 4H) 11-216 piperidin- Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.15 (s, 1H), 7.88 (d, 1H), 7.79 (d, 1H), 3.29 (m, 4H), 3.05 (s, 3H). 2.86 (s, 3H), 1.60 (broad, 6H). 11-217 piperidin- Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl 11.32 (s, 1H), 8.15 (d, 1H), 7.87 (d, 1H), 3.48 (s, 3H), 3.29 (m, 4H), 1.59 (broad, 6H). 11-218 NO₂ Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.29 (s, 1H), 7.91 (d, 1H), 7.82 (d, 1H), 3.06 (s, 3H), 2.87 (s, 3H) 11-219 NH₂ Cl (tetrahydrofuran-2- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz ylmethoxy)methyl 11.31 (s, 1H), 8.12 (d, 1H), 8.00 (d, 1H), 6.12 (bs, 2H), 5.08 (m, 2H), 3.99 (m, 1H), 3.70 (q, 2H), 3.68-3.52 (m, 3H), 3.39 (s, 3H), 1.97-1.70 (m, 3H), 1.53 (m, 1H) 11-220 NH₂ Me 1,2,3-triazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.24 (s, 1H), 8.55 (s, 1H), 8.18 (d, 1H), 8.16 (d, 1H), 6.16 (bs, 2H), 3.14 (s, 3H), 1.90 (s, 3H) 11-221 CO₂Me F S(O)Me CF₃ 11-222 CO₂Me Cl (tetrahydrofuran-2- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz ylmethoxy)methyl 12.20 (s, 1H), 8.13 (d, 1H), 7.87 (d, 1H), 5.10 (s, 2H), 3.98 (m, 1H), 3.92 (s, 3H), 3.72 (q, 2H), 3.65-3.53 (m, 3H), 3.39 (s, 3H), 1.96-1.72 (m, 3H), 1.55 (m, 1H) 11-223 CO₂Me Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.09 (s, 1H), 8.07 (d, 1H), 7.75 (d, 1H), 3.94 (s, 3H), 3.44 (s, 3H), 2.49 (s, 3H) 11-224 CO₂Me Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.09 (s, 1H), 7.90 (d, 1H), 7.83 (d, 1H), 3.95 (s, 3H), 3.06 (s, 3H), 2.87 (s, 3H) 11-225 CO₂Me Cl 1H-pyrazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.25 (s, 1H), 8.24 (d, 1H), 8.08 (d, 1H), 8.04 (d, 1H), 7.88 (d, 1H), 6.60 (t, 1H), 3.93 (s, 3H), 3.17 (s, 3H). 11-226 CO₂Me Me F SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.08 (bs, 1H), 7.86 (t, 1H), 7.64 (d, 1H), 3.93 (s, 3H), 3.31 (s, 3H), 2.29 (d, 3H). 11-227 CO₂Me Me 1,2,4-Triazol-1-yl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.20 (s, 1H), 8.55 (s, 1H), 8.20 (d, 1H), 8.07 (d, 1H), 8.05 (s, 1H), 3.92 (s, 3H), 3.15 (s, 3H), 1.93 (s, 3H) 11-228 CO₂Me Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.17 (s, 1H), 8.18 (d, 1H), 7.87 (d, 1H), 3.94 (s, 3H), 3.48 (s, 3H). 11-229 CO₂Me Me Me SMe ¹H NMR, DMSO-d₆, 400 MHz 11.62 (s, 1H), 7.39 (d, 1H), 7.20 (d, 1H), 3.90 (s, 3H), 2.32 (s, 3H), 2.25 (s, 3H). 11-230 CO₂Me Cl Me Cl ¹H NMR, DMSO-d₆, 400 MHz 11.96 (s, 1H), 7.64 (d, 1H), 7.48 (d, 1H), 3.92 (s, 3H), 2.49 (s, 3H) 11-231 CO₂Me Cl F Me ¹H NMR, DMSO-d₆, 400 MHz 11.89 (s, 1H), 7.62 (t, 1H), 7.45 (d, 1H), 3.92 (s, 3H), 2.36 (d, 3H). 11-232 CO₂Me Cl SMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.14 (s, 1H), 8.16 (d, 1H), 7.87 (d, 1H), 3.94 (s, 3H), 3.58 (s, 3H), 3.31 (s, 3H) 11-233 CO₂Et Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.14 (s, 1H), 8.07 (d, 1H), 7.96 (d, 1H), 4.42 (q, 2H), 3.43 (s, 3H), 3.75 (s, 3H), 1.34 (t, 3H) 11-234 CO₂H Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.87 (s, 1H), 8.06 (d, 1H), 7.96 (d, 1H), 3.43 (s, 3H), 2.75 (s, 3H) 11-235 piperidin- Cl 5-cyanomethyl-4,5- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 1-yl- dihydro-1,2-oxazol- 12.31 (s, 1H), 8.13 (d, 1H), 7.98 (d, 1H), carbonyl 3-yl 5.10 (m, 1H), 3.61 (dd, 1H), 3.44 (q, 2H), 3.05 (dd, 1H), 1.16 (t, 3H) 11-236 piperidin- Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl- 12.31 (s, 1H), 8.13 (d, 1H), 7.84 (d, 1H), carbonyl 5.22 (s, 2H), 4.29 (q, 2H), 3.59 (m, 2H), 3.40 (m, 2H), 3.37 (s, 3H), 1.6 (m, 6H) 11-237 piperidin- Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 1-yl- 12.24 (s, 1H), 8.04 (d, 1H), 7.93 (d, 1H), carbonyl 3.60 (m, 2H), 3.48 (m, 2H), 3.43 (s, 3H), 2.72 (s, 3H), 1.59 (m, 6H) 11-238 piperidin- Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 1-yl- 12.21 (s, 1H), 8.05 (d, 1H), 7.71 (d, 1H), carbonyl 3.60 (m, 2H), 3.46 (m, 2H), 3.43 (s, 3H), 1.68-1.52 (m, 6H) 11-239 SEt Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.75 (bs, 1H), 7.99 (d, 1H), 7.89 (d, 1H), 3.42 (s, 3H), 3.15 (q, 2H), 2.76 (s, 3H), 1.37 (t, 3H) 11-240 SPh Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.90 (s, 1H), 8.03 (d, 1H), 7.88 (d, 1H), 7.62 (m, 2H), 7.46 (m, 3H), 3.40 (s, 3H), 2.73 (s, 3H) 11-241 SO₂Me Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.00 (s, 1H), 8.08 (d, 1H), 7.95 (d, 1H), 3.69 (s, 3H), 3.43 (s, 3H), 2.77 (s, 3H) 11-242 Br Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.61 (s, 1H), 7.93 (d, 1H), 7.58 (d, 1H), 3.28 (s, 3H), 2.65 (s, 3H), 2.39 (s, 3H) 11-243 S(O)Me Me SO₂Me CF₃ 11-244 S(O)Me Me Me SO₂Me 11-245 c-Pr Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 11.50 (bs, 1H), 7.89 (s, 2H), 3.06 (s, 3H), 2.88 (s, 3H), 2.08 (m, 1H), 1.12 (m, 2H), 0.95 (m, 2H) 11-246 c-Pr Cl (tetrahydrofuran-2- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz ylmethoxy)methyl 11.63 (s, 1H), 8.11 (d, 1H), 7.94 (d, 1H), 5.11 (m, 2H), 3.98 (m, 1H), 3.71 (dd, 1H), 3.60 (m, 2H), 3.39 (s, 3H), 2.08 (m, 1H), 1.95-1.70 (m, 3H), 1.55 (m, 1H), 1.12 (mt, 2H), 0.96 (m, 2H) 11-247 c-Pr Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.65 (s, 1H), 8.16 (d, 1H), 7.95 (d, 1H), 3.48 (s, 3H), 2.07 (m, 1H), 1.13 (m, 2H), 0.95 (m, 2H) 11-248 c-Pr Me Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 11.38 (s, 1H), 7.92 (d, 1H), 7.61 (d, 1H), 3.28 (s, 3H), 2.65 (s, 3H), 2.38 (s, 3H), 2.05 (m, 1H), 1.13 (m, 2H), 0.96 (m, 2H) 11-249 Bz Me SMe CF₃ 11-250 Bz Me S(O)Me CF₃ 11-251 Bz Me SO₂Me CF₃ 11-252 Bz Me SMe SO₂CH₃ 11-253 Bz Me S(O)Me SO₂CH₃ 11-254 Bz Me SO₂Me SO₂CH₃ 11-255 Bz F SMe CF₃ 11-256 Bz F S(O)Me CF₃ 11-257 Bz F SO₂Me CF₃

B. Formulation Examples

-   a) A dust is obtained by mixing 10 parts by weight of a compound of     the formula (I) and/or a salt thereof and 90 parts by weight of talc     as inert substance and comminuting the mixture in a hammer mill. -   b) A wettable powder which is readily dispersible in water is     obtained by mixing 25 parts by weight of a compound of the     formula (I) and/or a salt thereof, 64 parts by weight of     kaolin-containing quartz as inert substance, 10 parts by weight of     potassium lignosulfonate and 1 part by weight of sodium     oleoylmethyltaurinate as wetting agent and dispersant, and grinding     the mixture in a pinned-disk mill. -   c) A readily water-dispersible dispersion concentrate is obtained by     mixing 20 parts by weight of a compound of the formula (I) and/or a     salt thereof with 6 parts by weight of alkylphenol polyglycol ether     (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether     (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling     range for example about 255 to above 277° C.) and grinding the     mixture in a ball mill to a fineness of below 5 microns. -   d) An emulsifiable concentrate is obtained from 15 parts by weight     of a compound of the formula (I) and/or a salt thereof, 75 parts by     weight of cyclohexanone as solvent and 10 parts by weight of     oxethylated nonylphenol as emulsifier. -   e) Water-dispersible granules are obtained by mixing     -   75 parts by weight of a compound of the formula (I) and/or a         salt thereof,     -   10 parts by weight of calcium lignosulfonate,     -   5 parts by weight of sodium lauryl sulfate,     -   3 parts by weight of polyvinyl alcohol and     -   7 parts by weight of kaolin,     -   grinding the mixture in a pinned-disk mill, and granulating the         powder in a fluidized bed by spraying on water as granulating         liquid. -   f) Water-dispersible granules are also obtained by homogenizing and     precomminuting, in a colloid mill,     -   25 parts by weight of a compound of the formula (I) and/or a         salt thereof,     -   5 parts by weight of sodium         2,2′-dinaphthylmethane-6,6′-disulfonate,     -   2 parts by weight of sodium oleoylmethyltaurinate,     -   1 part by weight of polyvinyl alcohol,     -   17 parts by weight of calcium carbonate and     -   50 parts by weight of water,     -   subsequently grinding the mixture in a bead mill and atomizing         and drying the resulting suspension in a spray tower by means of         a single-substance nozzle.

C. Biological Examples 1. Pre-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous or dicotyledonous weed plants or crop plants are placed in wood-fiber pots in sandy loam and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied as aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with the addition of 0.2% of wetting agent to the surface of the covering soil. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a trial period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, for example compounds No. 1-119, 1-53, 1-148, 1-54, 1-12, 1-71, 2-56, 9-180 and 9-174 have in each case an activity of at least 80% against Echinochloa crusgalli and Veronica persica at an application rate of 80 g/ha. Compounds No. 1-51, 1-123, 1-148, 1-149, 1-54, 2-119 and 2-71 have in each case an activity of at least 80% against Abutilon theophrasti and Amaranthus retroflexus at an application rate of 80 g/ha. Compounds No. 6-120, 3-120 and 6-3 have an activity of at least 80% against Matricaria inodora and Veronica persica at an application rate of 80 g/ha.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants are placed in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed as aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with the addition of 0.2% of wetting agent onto the green parts of the plants. After the test plants have been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations is rated visually in comparison to untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, for example compounds No. 1-119, 1-51, 1-53, 1-123, 1-148, 1-54, 2-119, 1-127, 9-180, 9-174, 3-119, 6-120, 4-120, 3-120 and 9-200 have an activity of at least 80% against Amaranthus retroflexus and Viola tricolor at an application rate of 80 g/ha. Compounds No. 1-147, 1-71, 2-71 and 6-3 have an activity of in each case at least 80% against Abutilon theophrasti and Veronica persica at an application rate of 80 g/ha. 

1. A compound of the formula (I) and/or a salt thereof

in which R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl or heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, X and Z independently of one another are in each case nitro, halogen, cyano, formyl, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂, or heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen, Y is nitro, halogen, cyano, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, CO₂R¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-heteroaryl, O—(C₁-C₆)-alkyl-heterocyclyl, O—(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, tetrahydrofuranyloxymethyl, tetrahydrofuranylmethoxymethyl, O(CH₂)-3,5-dimethyl-1,2-oxazol-4-yl, O(CH₂)₂—O(3,5-dimethoxypyrimidin-2-yl, O(CH₂)-5-pyrrolidin-2-one, O(CH₂)-5-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, or heteroaryl or heterocyclyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, halogen and cyanomethyl, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the 12 last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, rhodano, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁵ is methyl or ethyl, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 2. The compound and/or salt as claimed in claim 1, wherein R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, a heterocycle selected from the group consisting of pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, benzisoxazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-triazol-3-yl, 1-ethylbenzimidazol-2-yl, 4-methylthiazol-2-yl, thiophen-2-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, isoxazol-2-yl, isoxazol-3-yl, oxazol-2-yl, oxazol-3-yl, pyrrol-2-yl, pyrrol-3-yl, imidazol-2-yl, imidazol-5-yl, imidazol-4-yl, pyrazol-3-yl, pyrazol-5-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-1-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-thiatriazol-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl and pyridazin-4-yl, which heterocycle is substituted by s radicals selected from the group consisting of methyl, methoxy and halogen, or phenyl which is substituted by s radicals selected from the group consisting of methyl, methoxy, trifluoromethyl and halogen, X and Z independently of each other are in each case nitro, halogen, cyano, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or 1,2,4-triazol-1-yl, Y is nitro, halogen, cyano, rhodano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², tetrahydrofuranyloxymethyl, tetrahydrofuranylmethoxymethyl, O(CH₂)-3,5-dimethyl-1,2-oxazol-4-yl, O(CH₂)₂—O(3,5-dimethoxypyrimidin-2-yl, O(CH₂)-5-pyrrolidin-2-one or O(CH₂)-5-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR^(S), OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR^(S), OCOR³, SCOR³, NR³COR³, CO₂R³, COSR³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 3. The compound and/or salt as claimed in claim 1, wherein R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halogen-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, X and Z independently of one another are in each case nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R² or 1,2,4-triazol-1-yl, Y is nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², tetrahydrofuranyloxymethyl, tetrahydrofuranylmethoxymethyl, O(CH₂)-3,5-dimethyl-1,2-oxazol-4-yl, O(CH₂)₂—O(3,5-dimethoxypyrimidin-2-yl, O(CH₂)-5-pyrrolidin-2-one or O(CH₂)-5-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the three last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R³ is hydrogen or (C₁-C₆)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 4. The compound and/or salt as claimed in claim 1, wherein R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, X and Z independently of one another are in each case nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R² or 1,2,4-triazol-1-yl, Y is S(O)_(n)R², 4,5-dihydro-1,2-oxazol-3-yl, 5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl or 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the three last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR³, R³ is hydrogen or (C₁-C₆)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 5. A herbicidal composition which comprises a herbicidally effective amount of at least one compound of the formula (I) and/or salt as claimed in claim
 1. 6. The herbicidal composition as claimed in claim 5 comprising a mixture with at least one formulation auxiliary.
 7. The herbicidal composition as claimed in claim 5, comprising at least one further pesticidally active compound selected from the group consisting of the insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
 8. The herbicidal composition as claimed in claim 7, comprising a safener.
 9. The herbicidal composition as claimed in claim 7, comprising a further herbicide.
 10. A method of controlling undesired plants comprising applying an effective amount of at least one compound of the formula (I) and/or salt as claimed in claim 1 to a plant and/or to a location of undesired plant growth.
 11. A herbicidal composition as claimed in claim 5 suitable for controlling undesirable plants.
 12. The composition as claimed in claim 11, wherein the compound of the formula (I) and/or salt is capable of being used for controlling unwanted plants in crops of useful plants.
 13. The composition as claimed in claim 12, wherein the useful plants are transgenic useful plants. 